Processes for producing trifluoroiodomethane and trifluoroacetyl iodide

ABSTRACT

The present disclosure provides a process for producing trifluoroiodomethane, the process comprising providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof, reacting the reactant stream in the presence of a first catalyst at a first reaction temperature from about 25° C. to about 400° C. to produce an intermediate product stream comprising trifluoroacetyl iodide, and reacting the intermediate product stream in the presence of a second catalyst at a second reaction temperature from about 200° C. to about 600° C. to produce a final product stream comprising the trifluoroiodomethane.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a U.S. Continuation Application of U.S.application Ser. No. 16/549,412, entitled PROCESSES FOR PRODUCINGTRIFLUOROIODOMETHANE AND TRIFLUOROACETYL IODIDE, filed Aug. 23, 2019,which claims the benefit under 35 U.S.C. § 119(e) of U.S. ProvisionalPatent Application No. 62/889,958, entitled PROCESSES FOR PRODUCINGTRIFLUOROIODOMETHANE AND TRIFLUOROACETYL IODIDE, filed on Aug. 21, 2019,U.S. Provisional Patent Application No. 62/835,918, entitled PROCESSESFOR PRODUCING TRIFLUOROIODOMETHANE AND TRIFLUOROACETYL IODIDE, filed onApr. 18, 2019, and U.S. Provisional Patent Application No. 62/722,561,entitled PROCESSES FOR PRODUCING TRIFLUOROIODOMETHANE ANDTRIFLUOROACETYL IODIDE, filed on Aug. 24, 2018, the entire disclosuresof which are expressly incorporated herein.

FIELD

The present disclosure relates to processes for producingtrifluoroiodomethane (CF₃I) and trifluoroacetyl iodide (CF₃COI).Specifically, the present disclosure relates to gas-phase processes forproducing trifluoroiodomethane and trifluoroacetyl iodide.

BACKGROUND

Trifluoroacetyl iodide (CF₃COI) is a compound that can be converted totrifluoroiodomethane (CF₃I). Trifluoroiodomethane (CF₃I), also known asperfluoromethyliodide, trifluoromethyl iodide, or iodotrifluoromethane,is a useful compound in commercial applications as a refrigerant or afire suppression agent, for example. Trifluoroiodomethane is a lowglobal warming potential molecule with negligible ozone depletionpotential. Trifluoroiodomethane can replace more environmentallydamaging materials.

Methods of preparing trifluoroacetyl iodide are known. For example, thearticle, “The Reactions of Metallic Salts of Acids with Halogens. PartI. The Reaction of Metal Trifluoroacetates with Iodine, Bromine, andChlorine,” R. N. Haszeldine, Journal of the Chemical Society, pp.584-587 (1951), describes a batch reaction of trifluoroacetyl chlorideand anhydrous hydrogen iodide without a catalyst for 8 hours at 120° C.to produce trifluoroacetyl iodide at a yield of about 62%. The pooryield and lengthy reaction times make it quite inefficient.

U.S. Pat. No. 7,196,236 (Mukhopadhyay et al.) discloses a catalyticprocess for producing trifluoroiodomethane using reactants comprising asource of iodine, at least a stoichiometric amount of oxygen, and areactant CF₃R, where R is selected from the group consisting of —COOH,—COX, —CHO, —COOR₂, AND —SO₂X, where R₂ is alkyl group and X is achlorine, bromine, or iodine. Hydrogen iodide, which may be produced bythe reaction, can be oxidized by the at least a stoichiometric amount ofoxygen, producing water and iodine for economic recycling.

U.S. Pat. No. 7,132,578 (Mukhopadhyay et al.) also discloses acatalytic, one-step process for producing trifluoroiodomethane fromtrifluoroacetyl chloride. However, the source of iodine is iodinefluoride (IF). In contrast to hydrogen iodide, iodine fluoride isrelatively unstable, decomposing above 0° C. to I₂ and IF₅. Iodinefluoride may also not be available in commercially useful quantities.

Some known methods of preparing trifluoroacetyl iodide includeliquid-phase processes. Liquid-phase processes can require solvents thatmust be separated out and disposed of. The extra steps required forseparation and disposal make the processes less efficient.

Thus, there is a need to develop a more efficient process that may bescaled to produce commercial quantities of trifluoroiodomethane fromrelatively inexpensive raw materials.

SUMMARY

The present disclosure provides gas-phase processes for producingtrifluoroiodomethane (CF₃I) and trifluoroacetyl iodide (CF₃COI).

In one embodiment, the present invention provides a gas-phase processfor producing trifluoroiodomethane. The process comprises providing areactant stream comprising hydrogen iodide and at least onetrifluoroacetyl halide selected from the group consisting oftrifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetylbromide, and combinations thereof, reacting the reactant stream in thepresence of a first catalyst at a first reaction temperature from about25° C. to about 400° C. to produce an intermediate product streamcomprising trifluoroacetyl iodide, and reacting the intermediate productstream in the presence of a second catalyst at a second reactiontemperature from about 200° C. to about 600° C. to produce a finalproduct stream comprising the trifluoroiodomethane.

In another embodiment, the present invention provides a gas-phaseprocess for producing trifluoroacetyl iodide. The process comprisesproviding a reactant stream comprising hydrogen iodide and at least onetrifluoroacetyl halide selected from the group consisting oftrifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetylbromide, and combinations thereof, and reacting the reactant stream inthe presence of a first catalyst at a reaction temperature from about25° C. to about 400° C. to produce a product stream comprising thetrifluoroacetyl iodide.

In another embodiment, the present invention provides a compositioncomprising at least 98 wt. % of trifluoroacetyl iodide, and from about 1ppm to about 20,000 ppm (about 2 wt. %) in total of compounds selectedfrom the group consisting of chlorotrifluoroethane, trifluoroacetylchloride, iodotrifluoromethane, trifluoroacetyl fluoride,hexafluoropropanone, trifluoroacetic acid and chlorotrifluoromethane.

In another embodiment, the present invention provides a compositioncomprising at least 99 wt. % of trifluoroiodomethane, from 1 ppm to 500ppm chlorotrifluoroethane, less than 500 ppm hexafluoroethane, less than500 ppm trifluoromethane, less than 100 ppm carbon monoxide, less than 1ppm hydrogen chloride and from 1 ppm to 500 ppm in total of compoundsselected from the group consisting of trifluoroacetyl fluoride,hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetylchloride.

In another embodiment, the present invention provides a gas-phaseprocess for producing trifluoroiodomethane. The process comprisesproviding a reactant stream comprising trifluoroacetyl iodide, andreacting the reactant stream in the presence of a catalyst at a reactiontemperature from about 200° C. to about 600° C. to produce a productstream comprising the trifluoroiodomethane.

The above mentioned and other features of the disclosure, and the mannerof attaining them, will become more apparent and will be betterunderstood by reference to the following description of embodimentstaken in conjunction with the accompanying drawings.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a process flow diagram showing a gas-phase process formanufacturing trifluoroacetyl iodide.

FIG. 2 is process flow diagram showing a two-step gas-phase process formanufacturing trifluoroiodomethane.

FIG. 3 is a process flow diagram showing a gas-phase process formanufacturing trifluoroiodomethane from trifluoroacetyl iodide.

DETAILED DESCRIPTION

The present disclosure provides processes for the manufacture oftrifluoroiodomethane and trifluoroacetyl iodide that producesurprisingly good process yields starting from hydrogen, iodine, and atrifluoroacetyl halide, such as trifluoroacetyl chloride. Such startingmaterials are relatively inexpensive and readily available in commercialquantities. The processes of this disclosure may be high-yielding,gas-phase processes that are amenable for the manufacture oftrifluoroiodomethane and trifluoroacetyl iodide on a commercial scale.The disclosed gas-phase processes require no solvents, further enhancingtheir commercial appeal.

As disclosed herein, the trifluoroiodomethane and trifluoroacetyl iodideare produced from a reactant stream comprising hydrogen iodide (HI) andtrifluoroacetyl halide (CF₃COX, X═Cl, Br or F). The hydrogen iodide andthe trifluoroacetyl halide are anhydrous. It is preferred that there beas little water in the reactant stream as possible because any water inthe reactant stream may hydrolyze some of the trifluoroacetyl halide andform the more thermodynamically favorable trifluoroacetic acid, ratherthan the desired trifluoroacetyl iodide.

The anhydrous hydrogen iodide is substantially free of water. That is,any water in the anhydrous hydrogen iodide is in an amount by weightless than about 500 parts per million, about 300 ppm, about 200 ppm,about 100 ppm, about 50 ppm, about 30 ppm, about 20 ppm, about 10 ppm,about 5 ppm, about 3 ppm, about 2 ppm, or about 1 ppm, or less than anyvalue defined between any two of the foregoing values. Preferably, theanhydrous hydrogen iodide comprises water by weight in an amount lessthan about 100 ppm. More preferably, the anhydrous hydrogen iodidecomprises water by weight in an amount less than about 10 ppm. Mostpreferably, the anhydrous hydrogen iodide comprises water by weight inan amount less than about 1 ppm.

The reactant stream is substantially free of oxygen. That is, any oxygenin the reactant stream is in an amount by weight less than about 500parts per million, about 300 ppm, about 200 ppm, about 100 ppm, about 50ppm, about 30 ppm, about 20 ppm, about 10 ppm, about 5 ppm, about 3 ppm,about 2 ppm, or about 1 ppm, or less than any value defined between anytwo of the foregoing values. Preferably, the amount of oxygen by weightin the reactant stream is less than about 100 ppm. More preferably, theamount of oxygen by weight in the reactant stream is less than about 10ppm. Most preferably, the amount of oxygen by weight in the reactantstream is less than about 1 ppm. It is preferred that there be as littleoxygen in the reaction stream as possible because any oxygen in thereaction stream may oxidize at least some of the hydrogen iodide to formiodine and water before the hydrogen iodide can react to formtrifluoroacetyl iodide. Even if running with an excess of hydrogeniodide, the water formed may hydrolyze the trifluoroacetyl halide andform the more thermodynamically favorable trifluoroacetic acid, ratherthan the desired trifluoroiodomethane, reducing the efficiency of theprocess.

The at least one trifluoroacetyl halide is selected from the groupconsisting of trifluoroacetyl fluoride (CF₃COF), trifluoroacetylchloride (CF₃COCl), trifluoroacetyl bromide (CF₃COBr), and anycombinations thereof. Preferably, the at least one trifluoroacetylhalide comprises trifluoroacetyl chloride. More preferably, the at leastone trifluoroacetyl halide consists essentially of trifluoroacetylchloride. Most preferably, the at least one trifluoroacetyl halideconsists of trifluoroacetyl chloride.

Trifluoroacetyl chloride, for example, is readily available incommercial quantities from Sigma-Aldrich Corp., St. Louis, Mo.,Halocarbon Products Corporation, Peachtree Corners, Ga., or from SolvayS.A., Brussels, Belgium, for example. Hydrogen iodide is commerciallyavailable or may be manufactured by, for example, reacting elementaliodine with hydrazine, distilling it from a solution of sodium iodideand phosphoric acid, or irradiating a mixture of hydrogen and elementaliodine at a wavelength of about 578 nanometers.

In the reactant stream, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide may be as low as about 0.1:1, about 0.2:1, about0.3:1, about 0.4:1, about 0.5:1, about 0.6:1, about 0.7:1, about 0.8:1,about 0.9:1, about 0.95:1, about 0.99:1, or about 1:1, or as high asabout 1.01:1, about 1.05:1, about 1.1:1, about 1.2:1, about 1.3:1, about1.4:1, about 1.5:1, about 1.6:1, about 1.8:1, about 2.0:1, about 4.0:1,about 6.0:1, about 8.0:1, or about 10.0:1, or within any range definedbetween any two of the foregoing values, such as about 0.1:1 to about10.0:1, about 0.2:1 to about 8.0:1, about 0.3:1 to about 6.0:1, about0.4:1 to about 4.0:1, 0.5:1 to about 2.0:1, about 0.6:1 to about 1.2:1,about 0.7:1 to about 1.0:1, about 0.1:1 to about 2.0:1, about 0.5:1 toabout 1.5:1, about 0.6:1 to about 1.4:1, about 0.7:1 to about 1.3:1,about 0.8:1 to about 1.2:1, about 0.9:1 to about 1.1:1, about 0.95:1 toabout 1.05:1, about 0.99:1 to about 1.01:1, about 1:1 to about 2:1,about 0.8:1 to about 1.5:1, or about 0.95:1 to about 1.2:1, for example.Preferably, the mole ratio of the hydrogen iodide to the trifluoroacetylhalide may be from about 0.5:1 to about 2.0:1. More preferably, the moleratio of the hydrogen iodide to the trifluoroacetyl halide may be fromabout 0.6:1 to about 1.2:1. Most preferably, the mole ratio of thehydrogen iodide to the trifluoroacetyl halide may be from about 0.7:1 toabout 1.0:1.

The trifluoroacetyl halide and the hydrogen iodide forming the reactantstream may be individually pre-heated or pre-heated together beforeentering the reactor. The reactant stream may be pre-heated to atemperature as low as about 20° C., about 30° C., about 40° C., about50° C., about 60° C., or about 70° C., or to a temperature as high asabout 80° C., about 90° C., about 100° C., about 110° C., or about 120°C., or to a temperature within any range defined between any two of theforegoing values, such as about 30° C. to about 120° C., about 40° C. toabout 110° C., about 50° C. to about 100° C., about 60° C. to about 90°C., or about 70° C. to about 80° C., for example. Preferably, thereactant stream may be pre-heated to a temperature from about 40° C. toabout 120° C. More preferably, the reactant stream may be pre-heated toa temperature from about 60° C. to about 110° C. Most preferably, thereactant stream may be pre-heated to a temperature from about 80° C. toabout 100° C.

The hydrogen iodide and the trifluoroacetyl halide in the reactantstream react within a first reactor to produce an intermediate productstream comprising trifluoroacetyl iodide (CF₃COI) and at least onehydrogen halide (HX) by-product according to Equation 1 below:

HI+CF₃COX→CF₃COI+HX.  Eq. 1:

The at least one hydrogen halide is selected from the group consistingof hydrogen fluoride (HF), hydrogen chloride (HCl), and hydrogen bromide(HBr).

The first reactor may be a heated tube reactor comprising a tube made ofa metal such as stainless steel, nickel, and/or a nickel alloy, such asa nickel-chromium alloy, a nickel-molybdenum alloy, anickel-chromium-molybdenum alloy, or a nickel-copper alloy. The tubewithin the first reactor may be heated. The first reactor may be anytype of packed bed reactor.

The hydrogen iodide and the trifluoroacetyl halide in the reactantstream reacts in the presence of a first catalyst contained within thefirst reactor. The first catalyst may comprise activated carbon, mesocarbon, stainless steel, nickel, nickel-chromium alloy,nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina,platinum, palladium, or carbides, such as metal carbides, such as ironcarbide, molybdenum carbide and nickel carbide, and non-metal carbides,such as silicon carbide, or combinations thereof. The first catalyst maybe in the form of a mesh, pellet, or sphere, contained within the firstreactor. The first catalyst may have an average diameter ranging fromabout 1 mm to about 25 mm.

If the first catalyst comprises platinum and/or palladium, the firstcatalyst may be in the form of platinum and/or palladium on a support.The support for the first catalyst may comprise alumina or carbon. Theamount of platinum and/or palladium on the support, as a percentage ofthe total combined weight of the platinum and/or palladium and thesupport may be as little as about 0.01 weight percent (wt. %), about 0.1wt. %, about 0.3 wt. %, about 0.5 wt. %, about 0.7 wt. %, about 1 wt. %,about 2 wt. %, or about 3 wt. % or as great as about 4 wt. %, about 5wt. %, about 6 wt. %, about 8 wt. %, or about 10 wt. %, or within anyrange defined between any two of the foregoing values, such as about0.01 wt. % to about 10 wt. %, about 0.1 wt. % to about 10 wt. %, about0.5 wt. % to about 8 wt. %, about 1 wt. % to about 6 wt. %, about 2 wt.% to about 5 wt. %, about 3 wt. % to about 4 wt. %, about 2 wt. % toabout 3 wt. %, or about 0.5 wt. % to about 5 wt. %, for example.Preferably, the amount of platinum and/or palladium on the support maybe from about 0.1 wt. % to about 1 wt. %. More preferably, the amount ofplatinum and/or palladium on the support may be from about 0.3 wt. % toabout 0.7 wt. %. Most preferably, the amount of platinum and/orpalladium on the support may be about 0.5 wt. %.

Preferably, the first catalyst comprises activated carbon, meso carbon,stainless steel, platinum on a support, palladium on a support, orcarbides, such as metal carbides and non-metal carbides, such as siliconcarbide, or combinations thereof. More preferably, the first catalystcomprises platinum on a support, palladium on a support, activatedcarbon, silicon carbide, or combinations thereof. Most preferably, thefirst catalyst comprises activated carbon or silicon carbide.

Alternatively, the first catalyst may consist of surfaces of the firstreactor itself in contact with the reactant stream. The surfaces mayprovide a catalytic effect without the need for an additional catalyst.

The reactant stream may be in contact with the first catalyst for acontact time as short as about 0.1 seconds, 0.5 seconds, about 1 second,about 2 seconds, about 3 seconds, about 5 seconds, about 8 seconds,about 10 seconds, about 12 seconds, or about 15, about 18 seconds, or aslong as about 20 seconds, about 25 seconds, about 30 seconds, about 35seconds, about 40 seconds, about 50 seconds, about 60 seconds, about 80seconds, or about 300 seconds, or for any contact time within any rangedefined between any two of the foregoing values, such as about 0.1seconds to about 300 seconds, about 0.5 seconds to about 80 seconds,about 1 second to about 60 seconds, about 5 seconds to about 50 seconds,about 8 seconds to about 40 seconds, about 10 seconds to about 35seconds, about 12 seconds to about 30 seconds, about 15 seconds to about25 seconds, about 18 seconds to about 20 seconds, about 10 seconds toabout 40 seconds, or about 10 seconds to about 30 seconds, for example.Preferably, the reactant stream may be in contact with the firstcatalyst for a contact time from about 5 seconds to about 60 seconds.More preferably, the reactant stream may be in contact with the firstcatalyst for a contact time from about 10 seconds to about 40 seconds.Most preferably, the reactant stream may be in contact with the firstcatalyst for a contact time from about 15 seconds to about 35 seconds.

The reaction may be maintained at a first reaction operating pressure aslow as about atmospheric pressure, about 5 psig (34 kPaG), about 10 psig(69 kPaG), about 15 psig (103 kPaG), about 20 psig (138 kPaG), about 25psig (172 kPaG), about 30 psig (207 kPaG), about 35 psig (241 kPaG), orabout 40 psig (276 kPaG), or as high as about 50 psig (345 kPaG), about60 psig (414 kPaG), about 70 psig (483 kPaG), about 80 psig (552 kPaG),about 100 psig (689 kPaG), about 150 psig (1,034 kPaG), about 200 psig(1,379 kPaG), about 250 psig (1,724 kPaG), or about 300 psig (2,068KPaG), or within any range defined between any two of the foregoingvalues, such as about atmospheric pressure to about 300 psig (2,068KPaG), about 5 psig (34 kPaG) to about 250 psig (1,724 kPaG), about 10psig (69 kPaG) to about 200 psig (1,379 kPaG), about 15 psig (103 kPaG)to about 150 psig (1,034 kPaG), about 20 psig (138 kPaG) to about 100psig (689 kPaG), about 25 psig (172 kPaG) to about 80 psig (552 kPaG),about 30 psig (207 kPaG) to about 70 psig (483 kPaG), about 35 psig (241kPaG) to about 60 psig (414 kPaG), about 40 psig (276 kPaG) to about 50psig (345 kPaG), or about 140 kPaG to about 200 kPaG, for example.Preferably, the first reaction operation pressure is from about 5 psig(34 kPaG) to about 200 psig (1,379 kPaG). More preferably, the firstreaction operating pressure is from about 10 psig (69 kPaG) to about 150psig (1,034 kPaG). Most preferably, the first reaction operatingpressure is from about 20 psig (138 kPaG) to about 100 psig (689 kPaG).

In addition to trifluoroacetyl iodide and hydrogen halide, theintermediate product stream further comprises unreacted trifluoroacetylhalide and hydrogen iodide. The intermediate product stream may furthercomprise small amounts of other organic compounds, such astrifluoroiodomethane (CF₃I), for example.

The composition of the organic compounds in the intermediate productstream may be measured as by gas chromatography (GC) and gaschromatography-mass spectroscopy (GC-MS) analyses. Peak areas providedby the GC analysis for each of the organic compounds can be combined toprovide a GC area percentage (GC area %) of the total organic compoundsfor each of the organic compounds as a measurement of the relativeconcentrations of the organic compounds in the intermediate productstream. The GC area % may be interpreted as equivalent to a weight %.

The concentration of unreacted trifluoroacetyl halide in theintermediate product stream, in GC area % of total organic compounds,may be as low as about 1%, about 3%, about 5%, about 10%, about 15%,about 20%, about 25%, about 30%, about 35%, about 40%, or about 45%, ormay be as high as about 50%, about 55%, about 60%, about 65%, about 70%,about 75%, about 80%, about 85%, or about 90%, or within any rangedefined between any two of the foregoing values, such as about 1% toabout 90%, about 5% to about 85%, about 10% to about 80%, about 15% toabout 75%, about 20% to about 70%, about 25% to about 65%, about 30% toabout 60%, about 35% to about 55%, about 40% to about 50%, about 1% toabout 3%, about 5% to about 40% or about 5% to about 60%, for example.Preferably, the concentration of unreacted trifluoroacetyl halide in theintermediate product stream may be from about 1% to about 50%. Morepreferably, the concentration of unreacted trifluoroacetyl halide in theintermediate product stream may be from about 1% to about 40%. Mostpreferably, the concentration of unreacted trifluoroacetyl halide in theintermediate product stream may be from about 1% to about 30%.

The concentration of organic compounds in the intermediate productstream excluding trifluoroacetyl halide, trifluoroacetyl iodide andtrifluoroiodomethane, in GC area % of total organic compounds, may beless than about 15%, about 14%, about 13%, about 12%, about 11%, about10%, about 9%, about 8%, about 7%, about 6%, about 5%, about 4%, about3%, about 2%, about 1%, about 0.5%, or about 0.1%. Preferably, theconcentration of all other organic compounds in the intermediate productstream may be less than about 8%. More preferably, the concentration ofall other organic compounds in the intermediate product stream may beless than about 4%. Most preferably, the concentration of all otherorganic compounds in the intermediate product stream may be less thanabout 2%.

The reaction stream may be heated to a first reaction temperature as lowas about 25° C., about 30° C., about 40° C., about 50° C., about 60° C.,about 70° C., about 80° C., about 90° C., about 100° C., or about 120°C., or as high as about 150° C., about 180° C., about 200° C., about220° C., about 230° C., about 250° C., about 300° C., about 360° C., orabout 400° C. or to a first reaction temperature within any rangedefined between any two of the foregoing values, such as about 25° C. toabout 400° C., about 30° C. to about 360° C., about 40° C. to about 300°C., about 50° C. to about 280° C., about 60° C. to about 250° C., about70° C. to about 230° C., about 80° C. to about 220° C., about 90° C. toabout 200° C., about 100° C. to about 180° C., or about 110° C. to about150° C., for example.

In general, the conversion of trifluoroacetyl halide can be controlledthrough the selection of the catalyst, the first reaction temperature,the mole ratio of the hydrogen iodide to the trifluoroacetyl halide, andthe contact time.

Although the reaction can be carried out at a first reaction temperaturefrom about 25° C. to about 400° C., it has been found that a lowerreaction temperature, such as a first reaction temperature at or belowabout 120° C., the reaction can produce a low concentration oftrifluoroiodomethane in the intermediate product stream. Althoughtrifluoroiodomethane can be the final product desired, the presence oftrifluoroiodomethane in the intermediate product stream can reduce theoverall efficiency of the process because the trifluoroiodomethane canform an azeotrope with the trifluoroacetyl halide, such astrifluoroacetyl chloride, for example. The azeotrope can make itdifficult to separate the trifluoroiodomethane from the trifluoroacetylchloride, resulting in the loss of the trifluoroiodomethane.

It has been found that at first reaction temperatures at or below about120° C., a concentration of trifluoroiodomethane in the intermediateproduct stream can be less than 0.002%, or about 20 ppm, of the totalorganic compounds. For less than about 0.002% GC area % oftrifluoroiodomethane in the intermediate product stream, the reactionstream may be heated to a first reaction temperature as low as about 25°C., about 30° C., about 35° C., about 40° C., about 45° C., about 50°C., about 55° C., about 60° C., about 65° C., or about 70° C., or to atemperature as high as about 75° C., about 80° C., about 85° C., about90° C., about 95° C., about 100° C., about 105° C., about 110° C., about115° C. or about 120° C. or to a first reaction temperature within anyrange defined between any two of the foregoing values, such as about 25°C. to about 120° C., about 30° C. to about 115° C., about 35° C. toabout 110° C., about 40° C. to about 105° C., about 45° C. to about 100°C., about 50° C. to about 95° C., about 55° C. to about 90° C., about60° C. to about 85° C., about 65° C. to about 80° C. or about 70° C. toabout 75° C., for example. Preferably, the reaction stream may be heatedto a first reaction temperature from about 40° C. to about 120° C. Morepreferably, the reaction stream may be heated to a first reactiontemperature from about 70° C. to about 100° C. Most preferably, thereaction stream may be heated to a first reaction temperature from about80° C. to about 100° C.

The concentration of trifluoroacetyl iodide in the intermediate productstream, in GC area % of total organic compounds, where the reactionstream has a reaction temperature at or below about 120° C., may be aslow as about 10%, about 20%, about 30%, about 35%, about 40%, about 45%,about 50%, about 55%, about 60%, about 65% or about 70%, or may be ashigh as about 75%, about 80%, about 85%, about 90%, about 95%, about97%, about 98%, or about 99% or within any range defined between any twoof the foregoing values, such as about 10% to about 99%, about 10% toabout 99%, about 30% to about 99%, about 35% to about 98%, about 40% toabout 97%, about 45% to about 95%, about 50% to about 90%, about 55% toabout 85%, about 60% to about 80%, about 65% to about 75%, about 50% toabout 60%, about 90% to about 99% or about 95% to about 99%, forexample. Preferably, the concentration of trifluoroacetyl iodide in theintermediate product stream may be from about 50% to about 99%. Morepreferably, the concentration of trifluoroacetyl iodide in theintermediate product stream may be from about 60% to about 99%. Mostpreferably, the concentration of trifluoroacetyl iodide in theintermediate product stream may be from about 70% to about 99%.

The concentration of trifluoroiodomethane in the intermediate productstream, in GC area % of total organic compounds, where the reactionstream has a reaction temperature at or below about 120° C., may be lessthan about 0.010%, less than about 0.005%, less than about 0.002%, lessthan about 0.001%, less than about 0.0005%, less than about 0.0002%, orless than about 0.0001%, or less than any value defined between any twoof the foregoing values. Preferably, the concentration oftrifluoroiodomethane in the intermediate product stream may be less thanabout 0.002%. More preferably, the concentration of trifluoroiodomethanein the intermediate product stream may be less than about 0.001%. Mostpreferably, the concentration of trifluoroiodomethane in theintermediate product stream may be less than about 0.0005%.

Alternatively stated, organic compounds in the intermediate productstream, where the reaction stream has a first reaction temperature at orbelow about 120° C., may comprise, in GC area % of total organiccompounds, from about 10% to about 99% trifluoroacetyl iodide, fromabout 1% to about 90% unreacted trifluoroacetyl halide, less than about0.010% trifluoroiodomethane, and less than about 15% organic compoundsother than trifluoroacetyl iodide, trifluoroacetyl halide, andtrifluoroiodomethane. It is also provided that organic compounds in theintermediate product stream may comprise from about 50% to about 99%trifluoroacetyl iodide, from about 1% to about 50% unreactedtrifluoroacetyl halide, less than about 0.002% trifluoroiodomethane, andless than about 8% organic compounds other than trifluoroacetyl iodide,trifluoroacetyl halide, and trifluoroiodomethane. It is also providedthat organic compounds in the intermediate product stream may comprisefrom about 60% to about 99% trifluoroacetyl iodide, from about 1% toabout 40% unreacted trifluoroacetyl halide, less than about 0.001%trifluoroiodomethane, and less than about 4% organic compounds otherthan trifluoroacetyl iodide, trifluoroacetyl halide, andtrifluoroiodomethane. It is also provided that organic compounds in theintermediate product stream may comprise from about 70% to about 99%trifluoroacetyl iodide, from about 1% to about 30% unreactedtrifluoroacetyl halide, less than about 0.0005% trifluoroiodomethane,and less than about 2% organic compounds other than trifluoroacetyliodide, trifluoroacetyl halide, and trifluoroiodomethane.

Alternatively stated, organic compounds in the intermediate productstream, where the reaction stream has a first reaction temperature at orbelow about 120° C., may consist essentially of, in GC area % of totalorganic compounds, from about 10% to about 99% trifluoroacetyl iodide,from about 1% to about 90% unreacted trifluoroacetyl halide, less thanabout 0.010% trifluoroiodomethane, and less than about 15% organiccompounds other than trifluoroacetyl iodide, trifluoroacetyl halide, andtrifluoroiodomethane. It is also provided that organic compounds in theintermediate product stream may consist essentially of from about 50% toabout 99% trifluoroacetyl iodide, from about 1% to about 50% unreactedtrifluoroacetyl halide, less than about 0.002% trifluoroiodomethane, andless than about 8% organic compounds other than trifluoroacetyl iodide,trifluoroacetyl halide, and trifluoroiodomethane. It is also providedthat organic compounds in the intermediate product stream may consistessentially of from about 60% to about 99% trifluoroacetyl iodide, fromabout 1% to about 40% unreacted trifluoroacetyl halide, less than about0.001% trifluoroiodomethane, and less than about 4% organic compoundsother than trifluoroacetyl iodide, trifluoroacetyl halide, andtrifluoroiodomethane. It is also provided that organic compounds in theintermediate product stream may consist essentially of from about 70% toabout 99% trifluoroacetyl iodide, from about 1% to about 30% unreactedtrifluoroacetyl halide, less than about 0.0005% trifluoroiodomethane,and less than about 2% organic compounds other than trifluoroacetyliodide, trifluoroacetyl halide, and trifluoroiodomethane.

Alternatively stated, organic compounds in the intermediate productstream, where the reaction stream has a first reaction temperature at orbelow about 120° C., may consist of, in GC area % of total organiccompounds, from about 10% to about 99% trifluoroacetyl iodide, fromabout 1% to about 90% unreacted trifluoroacetyl halide, less than about0.010% trifluoroiodomethane, and less than about 15% organic compoundsother than trifluoroacetyl iodide, trifluoroacetyl halide, andtrifluoroiodomethane. It is also provided that organic compounds in theintermediate product stream may consist of from about 50% to about 99%trifluoroacetyl iodide, from about 1% to about 50% unreactedtrifluoroacetyl halide, less than about 0.002% trifluoroiodomethane, andless than about 8% organic compounds other than trifluoroacetyl iodide,trifluoroacetyl halide, and trifluoroiodomethane. It is also providedthat organic compounds in the intermediate product stream may consist offrom about 60% to about 99% trifluoroacetyl iodide, from about 1% toabout 40% unreacted trifluoroacetyl halide, less than about 0.001%trifluoroiodomethane, and less than about 4% organic compounds otherthan trifluoroacetyl iodide, trifluoroacetyl halide, andtrifluoroiodomethane. It is also provided that organic compounds in theintermediate product stream may consist of from about 70% to about 99%trifluoroacetyl iodide, from about 1% to about 30% unreactedtrifluoroacetyl halide, less than about 0.0005% trifluoroiodomethane,and less than about 2% organic compounds other than trifluoroacetyliodide, trifluoroacetyl halide, and trifluoroiodomethane.

The intermediate product stream may proceed directly to a firstdistillation column. Alternatively, the intermediate product stream maypass through a heat exchanger to cool the intermediate product streambefore the intermediate product stream is provided to the firstdistillation column.

The first distillation column is configured for the separation of someof the by-products, reactants, and organic compounds described abovefrom the trifluoroacetyl iodide to produce a purified intermediateproduct stream. The first distillation column may be configured toseparate and return the unreacted hydrogen iodide to the reactant streamand to separate and return the unreacted trifluoroacetyl halide to thereactant stream. The first distillation column may also be configured toseparate the hydrogen halide into a hydrogen halide stream for sale,reuse elsewhere, or disposal. The first distillation column may includea series of distillation columns, such as a hydrogen halide column toremove the hydrogen halide and light organics, a lights column to removethe unreacted trifluoroacetyl halide and the unreacted hydrogen iodidebefore sending them to a recycle column to separate the unreactedtrifluoroacetyl halide from the unreacted hydrogen iodide, and a heaviescolumn to purge heavy organics and produce the purified intermediateproduct stream.

The concentration of the trifluoroacetyl iodide in the purifiedintermediate product stream may be greater than about 98 weight percent(wt. %). Preferably, the concentration of the trifluoroacetyl iodide inthe purified intermediate product stream may be greater than about 99wt. %. More preferably, the concentration of the trifluoroacetyl iodidein the purified intermediate product stream may be greater than about99.5 wt. %. Most preferably, the concentration of the trifluoroacetyliodide in the purified intermediate product stream may be greater thanabout 99.7 wt. %.

The concentration of some impurities in the purified intermediateproduct stream may detract from the further use of the trifluoroacetyliodide. Thus, if the trifluoroacetyl halide in the reactant streamincludes trifluoroacetyl chloride, the purified intermediate productstream includes from about 1 ppm (part per million by weight) to about20,000 ppm (about 2 wt. %) in total of compounds selected from the groupconsisting of chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane. Preferably, thepurified intermediate product stream includes from about 1 ppm to about10,000 ppm (about 1 wt. %) in total of compounds selected from the groupconsisting of chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane. More preferably, thepurified intermediate product stream includes from about 1 ppm to about5,000 ppm in total of compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane. Most preferably, the purified intermediateproduct stream includes from about 1 ppm to about 3,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Alternatively stated, the purified intermediate product stream maycomprise at least 98 wt. % of trifluoroacetyl iodide, and from about 1ppm to about 20,000 ppm (about 2 wt. %) in total of compounds selectedfrom the group consisting of chlorotrifluoroethane, trifluoroacetylchloride, iodotrifluoromethane, trifluoroacetyl fluoride,hexafluoropropanone, trifluoroacetic acid and chlorotrifluoromethane. Itis also provided that the purified intermediate product stream maycomprise at least 99 wt. % of trifluoroacetyl iodide, and from 1 ppm to10,000 ppm (1 wt. %) in total of compounds selected from the groupconsisting of chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane. It is also providedthat the purified intermediate product stream may comprise at least 99.5wt. % of trifluoroacetyl iodide, and from 1 ppm to 5,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane. It is also provided that the purifiedintermediate product stream may comprise at least 99.7 wt. % oftrifluoroacetyl iodide, and from 1 ppm to 3,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Alternatively stated, the purified intermediate product stream mayconsist essentially of at least 98 wt. % of trifluoroacetyl iodide, andfrom about 1 ppm to about 20,000 ppm (about 2 wt. %) in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane. It is also provided that the purifiedintermediate product stream may consist essentially of at least 99 wt. %of trifluoroacetyl iodide, and from 1 ppm to 10,000 ppm (1 wt. %) intotal of compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane. It is also provided that the purifiedintermediate product stream may consist essentially of at least 99.5 wt.% of trifluoroacetyl iodide, and from 1 ppm to 5,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane. It is also provided that the purifiedintermediate product stream may consist essentially of at least 99.7 wt.% of trifluoroacetyl iodide, and from 1 ppm to 3,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Alternatively stated, the purified intermediate product stream mayconsist of at least 98 wt. % of trifluoroacetyl iodide, and from about 1ppm to about 20,000 ppm (about 2 wt. %) in total of compounds selectedfrom the group consisting of chlorotrifluoroethane, trifluoroacetylchloride, iodotrifluoromethane, trifluoroacetyl fluoride,hexafluoropropanone, trifluoroacetic acid and chlorotrifluoromethane. Itis also provided that the purified intermediate product stream mayconsist of at least 99 wt. % of trifluoroacetyl iodide, and from 1 ppmto 10,000 ppm (1 wt. %) in total of compounds selected from the groupconsisting of chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane. It is also providedthat the purified intermediate product stream may consist of at least99.5 wt. % of trifluoroacetyl iodide, and from 1 ppm to 5,000 ppm intotal of compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane. It is also provided that the purifiedintermediate product stream may consist of at least 99.7 wt. % oftrifluoroacetyl iodide, and from 1 ppm to 3,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

The purified intermediate product stream may be stored, or may beprovided to a second reactor for conversion into trifluoroiodomethane.The purified intermediate product stream comprising the trifluoroacetyliodide may be provided directly to the second reactor. Alternatively, oradditionally, the purified intermediate product stream may pass througha preheater to heat the purified intermediate product stream before thepurified intermediate product stream is provided to the second reactor.

The trifluoroacetyl iodide in the purified intermediate product streamreacts within the second reactor to produce a final product streamcomprising trifluoroiodomethane and reaction by-product carbon monoxide(CO) according to Equation 2 below:

CF₃COI→CF₃I+CO.  Eq. 2:

The second reactor may be a heated tube reactor comprising a tube madeof a metal such as stainless steel, nickel, and/or a nickel alloy, suchas a nickel-chromium alloy, a nickel-molybdenum alloy, anickel-chromium-molybdenum alloy, or a nickel-copper alloy. The tubewithin the second reactor may be heated. The second reactor may be anytype of packed bed reactor.

The purified intermediate product stream may be heated to a secondreaction temperature as low as about 200° C., about 250° C., about 300°C., about 310° C., about 320° C., about 325° C., about 330° C., about340° C., about 350° C., or about 360° C., or to a second reactiontemperature as high as about 370° C., about 380° C., about 390° C.,about 400° C., about 425° C., about 450° C., about 475° C., about 500°C., about 525° C., about 550° C., about 575° C., or about 600° C. or anyrange defined between any two of the foregoing values, such as about200° C. to about 600° C., about 250° C. to about 600° C., about 300° C.to about 600° C., about 320° C. to about 450° C., about 325° C. to about400° C., about 330° C. to about 390° C., about 340° C. to about 380° C.,about 350° C. to about 370° C., or about 340° C. to about 360° C., forexample. Preferably, the second catalyst may be heated to a secondreaction temperature from about 250° C. to about 500° C. Morepreferably, the second catalyst may be heated to a second reactiontemperature from about 300° C. to about 400° C. Most preferably, thesecond catalyst may be heated to a second reaction temperature fromabout 300° C. to about 350° C.

The trifluoroacetyl iodide in the purified intermediate product streammay react in the presence of a second catalyst contained within thesecond reactor. The second catalyst may comprise stainless steel,nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy,nickel-copper alloy, copper, alumina, silicon carbide, platinum,palladium, rhenium, activated carbon, such as such as Norit-PK35, Calgonor Shirasagi carbon, or combinations thereof. The second catalyst may bein the form of a mesh, pellet, or sphere, contained within the secondreactor. The second catalyst may have an average diameter ranging fromabout 1 mm to about 25 mm.

If the second catalyst comprises platinum, palladium, and/or rhenium,the second catalyst may be in the form of platinum, palladium, and/orrhenium on a support.

The support for the second catalyst may comprise alumina or carbon. Theamount of platinum, palladium, and/or rhenium on the support, as apercentage of the total combined weight of the platinum, palladium,and/or rhenium and the support may be as little as about 0.01 weightpercent (wt. %), about 0.1 wt. %, about 0.3 wt. %, about 0.5 wt. %,about 0.7 wt. %, about 1 wt. %, about 2 wt. %, or about 3 wt. % or asgreat as about 4 wt. %, about 5 wt. %, about 6 wt. %, about 8 wt. %, orabout 10 wt. %, or within any range defined between any two of theforegoing values, such as about 0.01 wt. % to about 10 wt. %, 0.1 wt. %to about 10 wt. %, about 0.5 wt. % to about 8 wt. %, about 1 wt. % toabout 6 wt. %, about 2 wt. % to about 5 wt. %, about 3 wt. % to about 4wt. %, about 2 wt. % to about 3 wt. %, or about 0.5 wt. % to about 5 wt.%, for example. Preferably, the amount of platinum, palladium, and/orrhenium on the support may be from about 0.1 wt. % to about 1 wt. %.More preferably, the amount of platinum, palladium, and/or rhenium onthe support may be from about 0.3 wt. % to about 0.7 wt. %. Mostpreferably, the amount of platinum, palladium, and/or rhenium on thesupport may be about 0.5 wt. %.

Preferably, the second catalyst comprises activated carbon, about 0.1wt. % to about 1 wt. % platinum on a support, about 0.1 wt. % to about 1wt. % palladium on a support, about 0.1 wt. % to about 1 wt. % rheniumon a support, or combinations thereof. More preferably, the secondcatalyst comprises activated carbon or about 0.3 wt. % to about 0.7 wt.% palladium on a support. Most preferably, the second catalyst comprisesactivated carbon.

The second catalyst may be an activated carbon, such as Norit-PK35,Calgon or Shirasagi carbon pellets or spheres, for example. Theactivated carbon may have a surface area as small as about 500 squaremeters per gram (m²/g), about 800 m²/g, about 850 m²/g, about 900 m²/g,about 950 m²/g, or about 1,000 m²/g, or as large as about 1,100 m²/g,about 1,200 m²/g, about 1,300 m²/g, about 1,400 m²/g, about 1,600 m²/g,about 1,800 m²/g, about 2,000 m²/g, or about 3,000 m²/g, or have asurface area within any range defined between any two of the foregoingvalues, such as about 500 m²/g to about 3,000 m²/g, about 800 m²/g toabout 2,000 m²/g, about 850 m²/g to about 1,800 m²/g, about 900 m²/g toabout 1,600 m²/g, about 950 m²/g to about 1,400 m²/g, about 1,000 m²/gto about 1,200 m²/g, or about 850 m²/g to about 1,300 m²/g, for example.

The activated carbon may have an average pore diameter as small as about0.2 nanometers (nm), about 0.5 nm, about 1 nm, about 1.5 nm, about 2 nm,or about 2.5 nm, or as large as about 3 nm, about 5 nm, about 10 nm,about 15 nm, about 20 nm, or about 25 nm, or an average pore diameterwithin any range defined between any two of the foregoing values, suchas about 0.2 nm to about 25 nm, about 0.2 nm to about 20 nm, about 1.0nm to about 15 nm, about 1.5 nm to about 10 nm, about 2 nm to about 5nm, or about 2.5 nm to about 3 nm, for example.

Alternatively, the second catalyst may consist of surfaces of the secondreactor itself in contact with the purified intermediate product stream,that is, an otherwise empty reactor. The surfaces may provide acatalytic effect without the need for an additional solid catalyst.

The purified intermediate product stream may be in contact with thesecond catalyst for a contact time as short as about 0.1 second, 1second, about 2 seconds, about 3 seconds, about 5 seconds, about 8seconds, about 10 seconds, about 12 seconds, or about 15 seconds, or aslong as about 18 seconds, 20 seconds, about 25 seconds, about 30seconds, about 35 seconds, about 40 seconds, about 50 seconds, about 60seconds, or about 300 seconds, or for any contact time within any rangedefined between any two of the foregoing values, such as about 0.1seconds to about 300 seconds, about 1 second to about 60 seconds, about3 seconds to about 50 seconds, about 5 seconds to about 40 seconds,about 8 seconds to about 35 seconds, about 10 seconds to about 30seconds, about 12 seconds to about 25 seconds, about 15 seconds to about20 seconds, about 20 seconds to about 25 seconds, about 10 seconds toabout 40 seconds, or about 10 seconds to about 30 seconds, for example.Preferably, the purified intermediate product stream may be in contactwith the second catalyst for a contact time from about 1 seconds toabout 60 seconds. More preferably, the purified intermediate productstream may be in contact with the second catalyst for a contact timefrom about 2 seconds to about 50 seconds. Most preferably, the purifiedintermediate product stream may be in contact with the second catalystfor a contact time from about 3 seconds to about 30 seconds.

The reaction may be maintained at a second reaction operating pressureas low as about atmospheric pressure, about 5 psig (34 kPaG), about 10psig (69 kPaG), about 15 psig (103 kPaG), about 20 psig (138 kPaG),about 25 psig (172 kPaG), about 30 psig (207 kPaG), about 35 psig (241kPaG), about 40 psig (276 kPaG) or about 50 psig (345 kPaG), or as highas about 60 psig (414 kPaG), about 70 psig (483 kPaG), about 80 psig(552 kPaG), about 100 psig (689 kPaG), about 120 psig (827 kPaG), about150 psig (1,034 kPaG), about 200 psig (1,379 kPaG), about 250 psig(1,724 kPaG), or about 300 psig (2,068 KPaG), or within any rangedefined between any two of the foregoing values, such as aboutatmospheric pressure to about 300 psig (2,068 KPaG), about 5 psig (34kPaG) to about 300 psig (2,068 KPaG), about 5 psig (34 kPaG) to about250 psig (1,724 kPaG), about 10 psig (69 kPaG) to about 200 psig (1,379kPaG), about 15 psig (103 kPaG) to about 150 psig (1,034 kPaG), about 20psig (138 kPaG) to about 120 psig (827 kPaG), about 25 psig (172 kPaG)to about 100 psig (689 kPaG), about 30 psig (207 kPaG) to about 80 psig(552 kPaG), about 35 psig (241 kPaG) to about 70 psig (483 kPaG), about40 psig (276 kPaG) to about 70 psig (483 kPaG), about 50 psig (345 kPaG)to about 60 psig (414 kPaG), 50 psig (345 kPaG) to about 250 psig (1,724kPaG), about 100 psig (689 kPaG) to about 200 psig (1,379 kPaG), orabout 150 psig (1,034 kPaG) to about 200 psig (1,379 kPaG), for example.

It has been found that the conversion rate of the trifluoroacetyl iodidemay be significantly improved by operating at pressures greater thanatmospheric pressure, even without the presence of the second catalyst.

The final product stream may proceed directly to a second distillationcolumn. Alternatively, the final product stream may pass through a heatexchanger to cool the final product stream before the final productstream is provided to the second distillation column.

The final product stream comprises a composition compromisingtrifluoroiodomethane and carbon monoxide by-product and unreactedtrifluoroacetyl iodide, as shown in Equation 2. The final product streamcomposition may further include residual impurities from the purifiedintermediate product stream, such as trifluoroacetyl chloride (CF₃COCl),and chlorotrifluoroethane (C₂H₂ClF₃), as well as byproducts, such astrifluoromethane (CHF₃), hexafluoroethane (C₂F₆), trifluoroacetylfluoride (CF₃COF), hexafluoropropanone (CF₃COCF₃), trifluoroacetaldehyde(CF₃COH), trifluorochloromethane (CF₃Cl), pentafluoroiodoethane (C₂F₅I),difluoroiodomethane (CHF₂I), pentafluoropropanone (CF₃COCHF₂),trifluoroacetic acid anhydride (CF₃COOCOCF₃), heptafluoroiodopropane(C₃F₇I), iodomethane (CH₃I), difluorochloroiodomethane (CClF₂I), and/ortrifluoroacetic acid (CF₃COOH).

The second distillation column is configured for the separation ofunreacted trifluoroacetyl iodide and by-products, such as carbonmonoxide, trifluoromethane and hexafluoroethane, from the final productstream composition. The second distillation column may be configured toseparate and return the unreacted trifluoroacetyl iodide to the purifiedintermediate product stream. The second distillation column may also beconfigured to separate the carbon monoxide into a carbon monoxide streamfor sale, reuse elsewhere, or disposal.

In addition to the trifluoroiodomethane, the final product streamcomposition comprises chlorotrifluoroethane, and may also includeresidual carbon monoxide and hydrogen halide. The third distillationcolumn is configured for the separation of some of thechlorotrifluoroethane from the trifluoroiodomethane. The thirddistillation column may also be configured for the separation ofresidual carbon monoxide and hydrogen chloride from thetrifluoroiodomethane to produce a purified final product composition.The second distillation column and the third distillation column mayinclude a series of distillation columns configured to additionallyremove such byproducts as trifluorochloromethane, pentafluoroiodoethane,difluoroiodomethane, pentafluoropropanone, trifluoroacetic acidanhydride, heptafluoroiodopropane, iodomethane,difluorochloroiodomethane, and/or trifluoroacetic acid, as well as someof trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride. The purified final product composition maybe directed to a storage tank.

The purified final product composition has a trifluoroiodomethaneconcentration greater than 99 wt. %. Preferably, the concentration ofthe trifluoroiodomethane in the purified final product composition maybe greater than 99.5 wt. %. More preferably, the concentration of thetrifluoroiodomethane in the purified final product composition may begreater than 99.7 wt. %. Most preferably, the concentration oftrifluoroiodomethane in the purified final product composition may begreater than 99.9 wt. %.

The concentration of some impurities in the purified final productstream may detract from the performance of the trifluoroiodomethane andits intended purpose as an environmentally safe, non-toxic gas. If thetrifluoroacetyl halide in the reactant stream includes trifluoroacetylchloride, the purified final product composition includes from 1 ppm(part per million by weight) to 500 ppm of chlorotrifluoroethane, lessthan 500 ppm hexafluoroethane, less than 500 ppm trifluoromethane, lessthan 100 ppm carbon monoxide, and less than 1 ppm hydrogen chloride. Itis preferred that the purified final product stream includes from 1 ppmto 250 ppm of chlorotrifluoroethane, less than 250 ppm hexafluoroethane,less than 250 ppm trifluoromethane, less than 50 ppm carbon monoxide,and less than 0.5 ppm hydrogen chloride. It is more preferred that thepurified final product stream includes from 1 ppm to 100 ppm ofchlorotrifluoroethane, less than 10 ppm hexafluoroethane, less than 100ppm trifluoromethane, less than 10 ppm carbon monoxide, and less than0.2 ppm hydrogen chloride.

The purified final product composition may further comprise in amountsfrom 1 ppm to 500 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride. It is preferredthat the purified final product composition further comprises in amountsfrom 1 ppm to 250 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride. It is morepreferred that the purified final product composition further comprisesin amounts from 1 ppm to 100 ppm in total of compounds selected from thegroup consisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Alternatively stated, if the trifluoroacetyl halide in the reactantstream includes trifluoroacetyl chloride, the purified final productcomposition may comprise at least 99 wt. % of trifluoroiodomethane, from1 ppm to 500 ppm chlorotrifluoroethane, less than 500 ppmhexafluoroethane, less than 500 ppm trifluoromethane, less than 100 ppmcarbon monoxide, less than 1 ppm hydrogen chloride and from 1 ppm to 500ppm in total of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride. It is also provided that the purifiedfinal product composition may comprise at least 99.5 wt. % oftrifluoroiodomethane, from 1 ppm to 250 ppm chlorotrifluoroethane, lessthan 250 ppm hexafluoroethane, less than 250 ppm trifluoromethane, lessthan 50 ppm carbon monoxide, less than 0.5 ppm hydrogen chloride andfrom 1 ppm to 250 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride. It is also providedthat the purified final product composition may comprise at least 99.7wt. % of trifluoroiodomethane, from 1 ppm to 100 ppmchlorotrifluoroethane, less than 100 ppm hexafluoroethane, less than 100ppm trifluoromethane, less than 20 ppm carbon monoxide, less than 0.2ppm hydrogen chloride and from 1 ppm to 100 ppm in total of compoundsselected from the group consisting of trifluoroacetyl fluoride,hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetylchloride. It is also provided that the purified final productcomposition may comprise at least 99.9 wt. % of trifluoroiodomethane,from 1 ppm to 100 ppm chlorotrifluoroethane, less than 100 ppmhexafluoroethane, less than 100 ppm trifluoromethane, less than 20 ppmcarbon monoxide, less than 0.2 ppm hydrogen chloride and from 1 ppm to100 ppm in total of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride.

Alternatively stated, if the trifluoroacetyl halide in the reactantstream includes trifluoroacetyl chloride, the purified final productcomposition may consist essentially of at least 99 wt. % oftrifluoroiodomethane, from 1 ppm to 500 ppm chlorotrifluoroethane, lessthan 500 ppm hexafluoroethane, less than 500 ppm trifluoromethane, lessthan 100 ppm carbon monoxide, less than 1 ppm hydrogen chloride and thebalance of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride. It is also provided that the purifiedfinal product composition may consist essentially of at least 99.5 wt. %of trifluoroiodomethane, from 1 ppm to 250 ppm chlorotrifluoroethane,less than 250 ppm hexafluoroethane, less than 250 ppm trifluoromethane,less than 50 ppm carbon monoxide, less than 0.5 ppm hydrogen chlorideand the balance of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride. It is also provided that the purifiedfinal product composition may consist essentially of at least 99.7 wt. %of trifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane,less than 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane,less than 20 ppm carbon monoxide, less than 0.2 ppm hydrogen chlorideand the balance of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride. It is also provided that the purifiedfinal product composition may consist essentially of at least 99.9 wt. %of trifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane,less than 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane,less than 100 ppm carbon monoxide, less than 0.2 ppm hydrogen chlorideand the balance of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride.

Alternatively stated, if the trifluoroacetyl halide in the reactantstream includes trifluoroacetyl chloride, the purified final productcomposition may consist of at least 99 wt. % of trifluoroiodomethane,from 1 ppm to 500 ppm chlorotrifluoroethane, less than 500 ppmhexafluoroethane, less than 500 ppm trifluoromethane, less than 100 ppmcarbon monoxide, less than 1 ppm hydrogen chloride and the balance ofcompounds selected from the group consisting of trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetaldehyde, andtrifluoroacetyl chloride. It is also provided that the purified finalproduct composition may consist of at least 99.5 wt. % oftrifluoroiodomethane, from 1 ppm to 250 ppm chlorotrifluoroethane, lessthan 250 ppm hexafluoroethane, less than 250 ppm trifluoromethane, lessthan 50 ppm carbon monoxide, less than 0.5 ppm hydrogen chloride and thebalance of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride. It is also provided that the purifiedfinal product composition may consist of at least 99.7 wt. % oftrifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane, lessthan 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane, lessthan 20 ppm carbon monoxide, less than 0.2 ppm hydrogen chloride and thebalance of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride. It is also provided that the purifiedfinal product composition may consist of at least 99.9 wt. % oftrifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane, lessthan 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane, lessthan 100 ppm carbon monoxide, less than 0.2 ppm hydrogen chloride andthe balance of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride.

It has been found that the purified final product stream of the two-stepgas-phase process described above results in a high-puritytrifluoroiodomethane product due to the high purity of thetrifluoroacetyl iodide in the purified intermediate product stream. Thetwo-step gas-phase process produces surprisingly good process yields andis amenable for the manufacture of trifluoroiodomethane on a commercialscale.

Alternatively, or additionally, a reactant stream includingtrifluoroacetyl iodide may be provided to the second reactor forconversion into trifluoroiodomethane as described above. The reactantstream including trifluoroacetyl iodide may be produced by processesother than those described above.

FIG. 1 is a process flow diagram showing a gas-phase process 10 formanufacturing trifluoroacetyl iodide. As shown in FIG. 1, the process 10comprises material flows of hydrogen iodide (HI) 12 and at least onetrifluoroacetyl halide, trifluoroacetyl chloride (CF₃COCl) 14. Althoughtrifluoroacetyl chloride is the trifluoroacetyl halide used toillustrate the processes of FIGS. 1-3, it is understood that thetrifluoroacetyl halide may alternatively, or additionally, betrifluoroacetyl bromide or trifluoroacetyl fluoride. The flow ofhydrogen iodide 12 and the flow of trifluoroacetyl chloride 14 arecombined in a mixer valve 16 to form a reactant stream 18. The reactantstream 18 may be provided directly to a reactor 20. Alternatively, thereactant stream 18 may pass through a preheater 22 to heat the reactantstream 18 before the reactant stream 18 is provided to the reactor 20.

The trifluoroacetyl chloride and the hydrogen iodide in the reactantstream 18 react in the presence of a catalyst 24 contained within thereactor 20 to produce a product stream 26 comprising trifluoroacetyliodide (CF₃COI) and hydrogen chloride (HCl) by-product according toEquation 1 above.

In addition to trifluoroacetyl iodide and hydrogen chloride, the productstream 26 further comprises unreacted trifluoroacetyl chloride andhydrogen iodide. The product stream 26 may even further comprise smallamounts of other organic compounds, such as trifluoroiodomethane (CF₃I).

The product stream 26 may proceed directly to a distillation column 28.Alternatively, the product stream 26 may pass through a heat exchanger30 before the product stream 26 is provided to the distillation column28, as shown in FIG. 1. The heat exchanger 30 is configured to cool theproduct stream 26 before it enters the distillation column 28.

The distillation column 28 is configured for the separation of some ofthe by-products, reactants, and organic compounds described above fromthe trifluoroacetyl iodide to produce a purified product stream 32. Asshown in FIG. 1, the distillation column 28 is configured to separateand return the unreacted hydrogen iodide to the flow of hydrogen iodide12 for use in the reactant stream 18 in a hydrogen iodide flow 36 and toseparate and return the unreacted trifluoroacetyl chloride to the flowof trifluoroacetyl chloride 14 for use in the reactant stream 18 in atrifluoroacetyl chloride flow 34.

The distillation column 28 is also configured to separate the hydrogenchloride into a hydrogen chloride waste stream 38 for sale, reuseelsewhere, or disposal. The purified product stream 32 comprising thetrifluoroacetyl iodide is directed to a storage tank 40.

It has been found that reacting hydrogen iodide and trifluoroacetylchloride in the presence of the catalyst 24 at the temperaturesdescribed above produces high conversion rates of the hydrogen iodideand trifluoroacetyl chloride with a high selectivity in favor oftrifluoroacetyl iodide. The gas-phase process described above inreference to Equation 1 produces surprisingly good process yields and isamenable for the production of trifluoroacetyl iodide on a commercialscale.

FIG. 2 is a process flow diagram showing two-step gas-phase process 110for manufacturing trifluoroiodomethane. As shown in FIG. 2, the process110 comprises material flows of hydrogen iodide (HI) 112 and at leastone trifluoroacetyl chloride (CF₃COCl) 114. The flow of hydrogen iodide112 and the flow of trifluoroacetyl chloride 114 are combined in a mixervalve 116 to form a reactant stream 118. The reactant stream 118 may beprovided directly to a first reactor 120. Alternatively, the reactantstream 118 may pass through a preheater 122 to heat the reactant stream118 before the reactant stream 118 is provided to the first reactor 120.

The trifluoroacetyl chloride and the hydrogen iodide in the reactantstream 118 react in the presence of a first catalyst 124 containedwithin the first reactor 120 to produce an intermediate product stream126 comprising trifluoroacetyl iodide (CF₃COI) and hydrogen chloride(HCl) by-product according to Equation 1 above.

In addition to trifluoroacetyl iodide and hydrogen chloride, theintermediate product stream 126 further comprises unreactedtrifluoroacetyl chloride and hydrogen iodide. The intermediate productstream 126 may even further comprise small amounts of other organiccompounds, such as trifluoroiodomethane (CF₃I), for example.

The intermediate product stream 126 may proceed directly to a firstdistillation column 128. Alternatively, the intermediate product stream126 may pass through a heat exchanger 130 before the intermediateproduct stream 126 is provided to the first distillation column 128, asshown in FIG. 2. The heat exchanger 130 is configured to cool theintermediate product stream 126 before it enters the first distillationcolumn 128.

The first distillation column 128 may be configured for the separationof some of the by-products, reactants, and organic compounds describedabove from the trifluoroacetyl iodide to produce a purified intermediateproduct stream 132. As shown in FIG. 2, the first distillation column128 is configured to separate and return the unreacted hydrogen iodideto the flow of hydrogen iodide 112 for use in the reactant stream 118 ina hydrogen iodide flow 134.

The first distillation column 128 is configured to separate and returnthe unreacted trifluoroacetyl chloride to the flow of trifluoroacetylchloride 114 for use in the reactant stream 118 in a trifluoroacetylchloride flow 136. The first distillation column 128 is also configuredto separate the hydrogen chloride into a hydrogen chloride stream 138for sale, reuse elsewhere, or disposal.

The purified intermediate product stream 132 may be provided directly toa second reactor 140, as shown in FIG. 2. Alternatively, the purifiedintermediate product stream 132 may pass through a preheater (not shown)to heat the purified intermediate product stream 132 before the purifiedintermediate product stream 132 is provided to the second reactor 140.

The trifluoroacetyl iodide in the purified intermediate product stream132 reacts in the presence of a second catalyst 142 contained within thesecond reactor 140 to produce a product stream 144 comprisingtrifluoroiodomethane and reaction by-product carbon monoxide (CO)according to Equation 2 above.

The product stream 144 may proceed directly to a second distillationcolumn 146, as shown in FIG. 2. Alternatively, the product stream 144may pass through a heat exchanger (not shown) before the product stream144 is provided to the second distillation column 146. The heatexchanger is configured to cool the product stream 144 before it entersthe second distillation column 146

In addition to the trifluoroiodomethane and carbon monoxide, the productstream 144 comprises unreacted trifluoroacetyl iodide and otherby-products, such as trifluoromethane (CHF₃), hexafluoroethane (C₂F₆),and chlorotrifluoroethane (C₂H₂ClF₃). The second distillation column 146is configured for the separation of unreacted trifluoroacetyl iodide andby-products, such as carbon monoxide, trifluoromethane andhexafluoroethane, from the trifluoroiodomethane to produce a purifiedproduct stream 148, comprising trifluoroiodomethane. As shown in FIG. 2,the second distillation column 146 may be configured to separate andreturn the unreacted trifluoroacetyl iodide to the purified intermediateproduct stream 132 in an unreacted trifluoroacetyl iodide flow 150. Thesecond distillation column 146 may also be configured to separate thecarbon monoxide into a carbon monoxide stream 152 for sale, reuseelsewhere, or disposal.

As shown in FIG. 2, the purified product stream 148 comprising thetrifluoroiodomethane is directed to a third distillation column 154 foradditional purification. In addition to the trifluoroiodomethane, thepurified product stream 148 includes chlorotrifluoroethane, and may alsoinclude residual carbon monoxide and hydrogen chloride. The thirddistillation column 154 is configured for the separation of thechlorotrifluoroethane from the trifluoroiodomethane to produce apurified final product stream 156 comprising trifluoroiodomethane. Asshown in FIG. 2, the third distillation column 154 may be configured toseparate the chlorotrifluoroethane into a chlorotrifluoroethane stream158 for sale, reuse elsewhere, or disposal. The third distillationcolumn 154 may also be configured to separate the carbon monoxide andhydrogen chloride into a waste stream 160 for disposal. The purifiedfinal product stream 156 comprising the trifluoroiodomethane may bedirected to a storage tank 162.

FIG. 3 is a process flow diagram showing a process 210 for manufacturingtrifluoroiodomethane from trifluoroacetyl iodide. The process 210 may beidentical to the second step of the two-step process described above andin reference to FIG. 2, except that the purified intermediate productstream 132 is replaced by a reactant stream 232. The reactant stream 232includes trifluoroacetyl iodide. The trifluoroacetyl iodide may beproduced by processes other than those described herein. The reactantstream 232 may further include trifluoroacetyl iodide produced byprocesses described herein.

While this invention has been described as relative to exemplarydesigns, the present invention may be further modified within the spiritand scope of this disclosure. Further, this application is intended tocover such departures from the present disclosure as come within knownor customary practice in the art to which this invention pertains.

As used herein, the phrase “within any range defined between any two ofthe foregoing values” literally means that any range may be selectedfrom any two of the values listed prior to such phrase regardless ofwhether the values are in the lower part of the listing or in the higherpart of the listing. For example, a pair of values may be selected fromtwo lower values, two higher values, or a lower value and a highervalue.

EXAMPLES Example 1: Manufacture of Trifluoroacetyl Iodide According toEquation 1 at Higher Reaction Temperatures

In this Example, the manufacture of trifluoroacetyl iodide from hydrogeniodide and trifluoroacetyl chloride according to Equation 1 at highertemperatures as described above is demonstrated. Equimolar amounts oftrifluoroacetyl chloride and anhydrous hydrogen iodide were passedthrough a preheater and heated to a temperature of about 100° C. in aseries of twenty-three experiments. The heated reactants were passedthrough a stainless-steel tube ⅜ inch (9.5 mm) in diameter and 6 inches(152 mm) in length. The tube was heated to temperatures ranging from200° C. to 350° C., depending on the experiment, and purged withnitrogen for at least one hour before each experiment to drive off anywater. In twenty-one experiments, the tube contained one of severalcatalysts. In the remaining two experiments, the tube did not contain acatalyst. Contact times were varied from 10 seconds to 30 seconds. Allexiting vapors for each experiment were collected in a sample bags forGC and GC-MS analyses. The results are shown in Tables 1, 2, and 3.

Table 1 lists the reaction conditions (temperature, contact time, andcatalyst used) for each of the twenty-three experiments. Table 2 liststhe GC area % of the primary organic compounds of interest correspondingto each of the twenty-three experiments. Table 3 lists a conversionpercentage and selectivity percentages for trifluoroiodomethane,trifluoroacetyl iodide, and the combination of trifluoroiodomethane andtrifluoroacetyl iodide corresponding to each of the twenty-threeexperiments. Conversion and selectivity percentages are based on the GCarea % data.

As shown in Tables 1, 2, and 3, the process described above in referenceto Equation 1 is able to produce trifluoroacetyl iodide with conversionpercentages exceeding 90% and selectivity percentages exceeding 99%.Thus, Tables 1, 2, and 3 demonstrate processes in accordance with thisdisclosure for the production of trifluoroacetyl iodide that producesurprisingly good results.

TABLE 1 Reaction Conditions Exper- Contact iment Temp. Time Number (°C.) (seconds) Catalyst 1 200 30 Empty Stainless-Steel Tube 2 350 20Empty Stainless-Steel Tube 3 200 30 ProPak ®-Stainless Steel 4 350 20ProPak ®-Stainless Steel 5 200 30 ProPak ®-Hastelloy C 6 350 20ProPak ®-Hastelloy C 7 200 30 Cu Mesh 8 350 20 Cu Mesh 9 200 30Activated Carbon-Shirasagi 10 350 20 Activated Carbon-Shirasagi 11 20030 Activated Carbon-PCP-LS 4 × 10 12 350 20 Activated Carbon-PCP-LS 4 ×11 13 200 30 Activated Carbon-X2M 4/6 14 350 20 Activated Carbon-X2M 4/715 200 30 Activated Carbon-Calgon Carbon 16 350 20 ActivatedCarbon-Calgon Carbon 17 200 30 Gamma Alumina 18 350 20 Gamma Alumina 19200 30 Activated Carbon, Norit-PK35 20 250 28 0.5% Pd on alumina 21 25032 0.5% Pd on alumina 22 225 10 Silicon carbide 23 200 10 Siliconcarbide

TABLE 2 Products GC Area % Experiment Others Number CHF₃ CF₃CI CF₃COCICF₃I CF₃COI (sum) 1 0.08 49.12 0.1 48.61 2.09 2 44.27 0.23 51.95 3.55 344.25 0.12 48.63 7 4 0.02 30.58 0.07 65.6 3.73 5 80.31 17.9 1.79 6 78.9918.14 2.87 7 0.02 72.49 23.59 3.9 8 0.02 58.02 39.03 2.93 9 0.03 94.293.8 1.88 10 2.3 58.22 31.37 6.18 1.93 11 91.29 0.18 6.2 2.33 12 35.0956.12 3.81 4.98 13 82.79 0.05 15.92 1.24 14 64.33 12.81 20.93 1.93 1580.9 0.2 14.25 4.65 16 1.75 55.51 26.09 12.3 4.35 17 35.61 0.26 52.2911.84 18 5.14 47.28 1.56 33.91 12.11 19 0.04 22.7 0.32 74.65 2.29 200.03 5.27 0.12 93.8 0.78 21 0.02 2.07 0.35 93.9 3.66 22 5.05 1.69 87.85.46 23 3.61 0.31 92.02 4.06

TABLE 3 Conv. % and Sel. % Sel. % Sel. % Sel. % Experiment Conv. CF₃ICF₃COI CF₃I + Number % Only Only CF₃COI 1 50.9 0.2 95.5 95.7 2 55.7 0.493.2 93.6 3 55.8 0.2 87.2 87.4 4 69.4 0.1 94.5 94.6 5 19.7 0.0 90.9 90.96 21.0 0.0 86.3 86.3 7 27.5 0.0 85.8 85.8 8 42.0 0.0 93.0 93.0 9 5.7 0.066.5 66.5 10 41.8 75.1 14.8 89.9 11 8.7 2.1 71.2 73.2 12 64.9 86.5 5.992.3 13 17.2 0.3 92.5 92.8 14 35.7 35.9 58.7 94.6 15 19.1 1.0 74.6 75.716 44.5 58.6 27.6 86.3 17 64.4 0.4 81.2 81.6 18 52.7 3.0 64.3 67.3 1977.3 0.4 96.6 97.0 20 94.7 0.1 99.0 99.1 21 97.9 0.4 95.9 96.2 22 95.01.8 92.5 94.2 23 96.4 0.3 95.5 95.8

Example 2: Manufacture of Trifluoroacetyl Iodide According to Equation 1at a Higher Reaction Temperature

In this Example, the manufacture of trifluoroacetyl iodide from hydrogeniodide and trifluoroacetyl chloride according to Equation 1 at a higherreaction temperature as described above is demonstrated. Trifluoroacetylchloride at flow rate of 8.34 g/hour of and hydrogen iodide at a flowrate of 14.08 g/hour were passed through a stainless-steel tube ⅜ inch(9.5 mm) in diameter and 6 inches (152 mm) in length. The tube washeated to about 300° C., and purged with nitrogen for at least one hourbefore the experiment to drive off any water. The tube contained acatalyst of Pro-Pak® stainless steel for a contact time of about 10seconds. The process was run continuously for 6.25 hours. The output ofthe reactor was collected in two dry ice traps, one at around 0° C. to−5° C. and the other at around −78° C.

A total of 99.8 g of material was collected and a portion analyzed by GCand GC-MS. The collected material was found to contain a mixture oftrifluoroacetyl iodide and trifluoroacetyl chloride in a 60:40 ratio.The selectivity of trifluoroacetyl iodide ranged from 88% to 97% basedon the GC area %.

Example 3: Manufacture of Trifluoroacetyl Iodide According to Equation 1at a Higher Reaction Temperature

In this Example, the manufacture of trifluoroacetyl iodide from hydrogeniodide and trifluoroacetyl chloride according to Equation 1 at a higherreaction temperature as described above is demonstrated. Trifluoroacetylchloride at flow rate of 5.75 g/hour of and hydrogen iodide at a flowrate of 13.9 g/hour were passed through a stainless-steel tube ½ inch(12.7 mm) in diameter and 6 inches (152 mm) in length. The tube washeated to about 250° C., and purged with nitrogen for at least one hourbefore the experiment to drive off any water. The tube contained acatalyst of 0.5% palladium on an alumina support (3.2 mm pellets) for acontact time of about 15 seconds. The process was run continuously for5.25 hours. The output of the reactor was collected in two dry icetraps, one at around 0° C. to −5° C. and the other at around −78° C.

A total of 89 g of material was collected and a portion analyzed byGC-MS. The collected material was found to contain a mixture oftrifluoroacetyl iodide and trifluoroacetyl chloride in a 70:30 ratio.Selectivity of trifluoroacetyl iodide to trifluoroiodomethane rangedfrom 92% to 98% based on the GC area %. This example was repeated with acatalyst of silicon carbide (3 mm pellets) with similar results

Example 4: Manufacture of Trifluoroacetyl Iodide According to Equation 1at Lower Reaction Temperatures

In this Example, the manufacture of trifluoroacetyl iodide from hydrogeniodide and trifluoroacetyl chloride according to Equation 1 at lowertemperatures as described above is demonstrated. Amounts oftrifluoroacetyl chloride and anhydrous hydrogen iodide in specific molarratios were passed through a metal tube ¾ inch (19.05 mm) in diameter. Apressure transducer and control valve at the outlet of the reactor wereused to control the pressure. The tube was heated to temperaturesranging from 40° C. to 210° C., depending on the experiment. Intwenty-six of the twenty-eight experiments, the tube contained one ofseveral catalysts. In the remaining two experiments, the tube did notcontain a catalyst. Contact times were varied from 6.1 seconds to 71.7seconds. The reactor effluent for each experiment passed through aheat-traced line to prevent condensation of the trifluoroacetyl iodideand directed to a dry-ice trap to capture the crude product. Uncondensedvapors escaping from the dry-ice trap were directed to a water scrubberand a caustic scrubber. Samples were taken from the reactor effluent forGC and GC-MS analyses. A contact time in the reactor was calculated foreach experiment based on the combined feed rates of the trifluoroacetylchloride and the hydrogen iodide. Run times ranged from 8 hours to 49hours. At the end of run time for the reaction for each experiment, thesystem was shut down and all containers were weighted to for massbalance purposes. The crude product collected in the dry-ice trap wasalso sampled and analyzed for GC and GC-MS analysis. The results areshown in Tables 4 and 5.

Table 4 lists the reaction conditions (temperature, mole ratio, contacttime, reactor type, pressure and catalyst used) for each of thetwenty-eight experiments. Table 5 lists the GC area % of the primaryorganic compounds of interest as well as a conversion percentage of thetrifluoroacetyl chloride and selectivity to trifluoroacetyl iodidecorresponding to each of the twenty-eight experiments. Conversion andselectivity percentages are based on the GC area % data.

As shown in Tables 4 and 5, the process described above in reference toEquation 1 operating at reaction temperatures at or below about 120° C.is able to produce trifluoroacetyl iodide with a concentration oftrifluoroiodomethane less than 0.002%, or about 20 ppm, of the totalorganic compounds with conversion percentages exceeding 80% (with acatalyst and with trifluoroacetyl chloride to hydrogen ratios aroundunity) and selectivity for trifluoroacetyl iodide of 99 mol % orgreater. Thus, Tables 4 and 5 demonstrate processes in accordance withthis disclosure for the production of trifluoroacetyl iodide thatproduce surprisingly good results.

TABLE 4 Reaction Conditions Exp. Temp. CF₃COCI:HI Contact Time ReactorTube No. (° C.) (mole ratio) (seconds) (Inconel Type) Pressure Catalyst1 210 0.99 21 600 0 None psig/kPaG 2 210 1.43 6.1 600 0 0.5% Pd/Al₂O₃psig/kPaG 3 210 1.12 6.8 600 0 Silicon Carbide (SiC2-E3-HP) psig/kPaG 4210 0.95 6.3 600 0 Silicon Carbide (SiC2-E3-HP) psig/kPaG 5 180 0.99 7.8600 0 Silicon Carbide (SiC2-E3-HP) psig/kPaG 6 150 0.99 8.4 600 0Silicon Carbide (SiC2-E3-HP) psig/kPaG 7 120 0.99 9.0 600 0 SiliconCarbide (SiC2-E3-HP) psig/kPaG 8 90 0.96 8.6 600 0 Silicon Carbide(SiC2-E3-HP) psig/kPaG 9 60 0.96 9.4 600 0 Silicon Carbide (SiC2-E3-HP)psig/kPaG 10 40 0.99 10.2 600 0 Silicon Carbide (SiC2-E3-HP) psig/kPaG11 60 0.99 12.9 600 5 psig Silicon Carbide (SiC2-E3-HP) (34.5 kPaG) 1260 0.99 19.4 600 15 psig Silicon Carbide (SiC2-E3-HP) (103 kPaG) 13 600.92 18.5 600 15 psig Activated Carbon (Norit ROX0.8) (103 kPaG) 14 900.92 17.0 600 15 psig Activated Carbon (Norit ROX0.8) (103 kPaG) 15 1200.92 15.7 600 15 psig Activated Carbon (Norit ROX0.8) (103 kPaG) 16 400.92 19.7 600 15 psig Activated Carbon (Norit ROX0.8) (103 kPaG) 17 600.79 18.0 600 15 psig Activated Carbon (CPG CF12X40) (103 kPaG) 18 900.79 16.5 600 15 psig Activated Carbon (CPG CF12X40) (103 kPaG) 19 600.80 16.5 600 15 psig Activated Carbon (OLC12X30) (103 kPaG) 20 90 0.8015.1 600 15 psig Activated Carbon (OLC12X30) (103 kPaG) 21 60 0.79 17.1600 15 psig Activated Carbon (JEChem C2X8/12) (103 kPaG) 22 90 0.79 15.7600 15 psig Activated Carbon (JEChem C2X8/12) (103 kPaG) 23 90 0.75 15.6600 15 psig Activated Carbon (Norit ROX0.8) (103 kPaG) 24 90 1.40 20.1600 15 psig Activated Carbon (Norit ROX0.8) (103 kPaG) 25 90 1.56 71.7625 15 psig None (103 kPaG) 26 90 1.43 22.3 625 20 psig Inconel 625 WireMesh (138 kPaG) 27 90 1.38 27.1 600 20 psig Silicon Carbide (SiC1-E3-P)(138 kPaG) 28 90 1.27 24.5 600 20 psig Silicon Carbide (SiC1-E3-HP) (138kPaG)

TABLE 5 Conversion Selectivity Exp. CF₃COCI CF₃I C₂H₂CIF₃ CF₃COI Othersof CF₃COCI of CF₃COI No. (GC area %) (GC area %) (GC area %) (GC area %)(GC area %) (mol %) (mol %) 1 56.22 0.002 0.037 38.90 4.84 43.46 2 21.450.43 0.024 73.79 4.31 78.01 3 18.89 2.91 0.012 76.41 1.78 81.90 4 18.033.22 0.017 75.73 3.00 81.38 5 17.11 0.25 0.022 79.99 2.63 82.77 6 17.440.012 0.027 80.71 1.81 82.49 7 16.56 0 0.037 81.63 1.77 83.37 8 11.27 00.026 83.13 5.57 88.30 9 12.35 0 0.027 83.70 3.92 87.59 10 12.81 0 0.02782.80 4.36 87.12 11 14.05 0 0.029 83.26 2.66 85.89 12 14.27 0 0.03083.51 2.19 85.69 13 14.59 0 0.031 83.57 1.81 85.34 14 12.55 0 0.02985.86 1.56 87.38 15 14.50 0.0014 0.032 82.36 3.11 85.22 16 20.85 0 0.03575.94 3.18 79.08 17 9.01 0 0.031 87.22 3.74 90.82 18 10.45 0 0.033 86.093.43 89.46 19 9.60 0 0.032 86.04 4.33 90.28 20 11.21 0 0.035 85.09 3.6788.70 21 11.06 0 0.036 85.31 3.59 88.86 22 10.62 0 0.036 86.16 3.1889.31 23 11.48 0 0.038 86.10 2.38 88.43 24 28.50 0 0.40 69.93 1.17 71.3825 62.36 0 0.069 35.30 2.27 37.56 26 66.36 0 0.072 30.82 2.75 33.5499.99 27 31.57 0 0.047 65.66 2.72 68.28 99.97 28 21.72 0 0.050 76.032.20 78.09 99.03

Example 5: Evaluation of SiC Catalyst Lifetime in the Manufacture ofTrifluoroacetyl Iodide According to Equation 1 at a Lower ReactionTemperature

In this Example, the lifetime of a silicon carbide catalyst (SiC1-E3-M)was evaluated in the manufacture of trifluoroacetyl iodide from hydrogeniodide and trifluoroacetyl chloride according to Equation 1 at 90° C. Inthis Example, 20 mL of the silicon carbide catalyst was loaded into anInconel 600 tube ¾ inch (19.05 mm) in diameter. A pressure transducerand control valve at the outlet of the reactor were used to control thepressure to 20 psig (138 kPaG). Periodically, the system was shut downto check the mass balance and collect the crude product for analysis.This was repeated for a series of five runs extending over a total runtime of over 455 hours. The results are shown in Table 6.

Table 6 lists the reaction conditions (mole ratio, contact time, time onstream and cumulative time on stream) for each of the five consecutiveruns. Table 6 also lists a conversion percentage of the trifluoroacetylchloride, selectivity to trifluoroacetyl iodide and the GC area % oftrifluoroiodomethane for each of the five consecutive runs. Conversionand selectivity percentages are based on GC area % data.

As shown in Table 6, the process described above in reference toEquation 1 operating at reaction temperatures at 90° C. is able toproduce trifluoroacetyl iodide with no detectable trifluoroiodomethaneformation. No deactivation of the silicon carbide catalyst was observedduring over 455 hours of operation.

TABLE 6 Contact Time On Total Time Conversion Selectivity Run.CF₃COCI:HI Time Stream On Stream of CF3COCI of CF3COI CF3I No. (moleratio) (seconds) (hrs) (hrs) (mol %) (mol %) (GC area %) 1 1.14 23.92 9696 77.92 99.96 0.00 2 1.25 24.67 96 192 74.99 99.95 0.00 3 1.32 24.50 96288 73.53 99.95 0.00 4 1.24 25.25 100 388 72.24 99.9 0.00 5 1.32 25.2467.25 455.25 81.75 99.91 0.00

Example 6: Evaluation of Activated Carbon Catalyst Lifetime in theManufacture of Trifluoroacetyl Iodide According to Equation 1 at a LowerReaction Temperature

In this Example, the lifetime of an activated carbon catalyst (NoritROX0.8) was evaluated in the manufacture of trifluoroacetyl iodide fromhydrogen iodide and trifluoroacetyl chloride according to Equation 1 at90° C. In this Example, 20 mL of the activated carbon catalyst wasloaded into an Inconel 600 tube ¾ inch (19.05 mm) in diameter. Apressure transducer and control valve at the outlet of the reactor wereused to control the pressure. Periodically, the system was shut down tocheck the mass balance and collect the crude product for analysis. Thiswas repeated for a series of twenty-nine runs extending over a total runtime of over 2,000 hours. The results are shown in Table 7.

Table 7 lists the reaction conditions (pressure, mole ratio, contacttime, time on stream and cumulative time on stream) for each of thetwenty-nine consecutive runs. Table 7 also lists a conversion percentageof the trifluoroacetyl chloride, selectivity to trifluoroacetyl iodideand the GC area % of trifluoroiodomethane for each of the twenty-nineconsecutive runs. Conversion and selectivity percentages are based on GCarea % data.

As shown in Table 7, the process described above in reference toEquation 1 operating at reaction temperatures at 90° C. is able toproduce trifluoroacetyl iodide with no detectable trifluoroiodomethaneformation. No deactivation of the activated carbon catalyst was observedduring over 2,051 hours of operation.

TABLE 7 Contact Time On Total Time Conversion Selectivity Run.CF₃COCI:HI Time Stream On Stream of CF3COCI of CF3COI CF3I No. Pressure(mole ratio) (seconds) (hrs) (hrs) (mol %) (mol %) (GC area %) 1 50 psig1.86 37.7 97.75 97.75 71.81 (345 kPaG) 2 50 psig 0.95 57.9 87.50 185.2594.03 (345 kPaG) 3 30 psig 1.36 28.1 42.75 228.00 78.88 (207 kPaG) 4 20psig 1.36 21.8 52.00 280.00 56.81 (138 kPaG) 5 20 psig 1.61 28.4 12.00292.00 55.68 (138 kPaG) 6 20 psig 1.47 24.2 93.25 385.25 70.05 99.890.00 (138 kPaG) 7 30 psig 1.32 30.7 98.50 483.75 70.49 99.95 0.00 (207kPaG) 8 30 psig 1.10 34.4 100.00 583.75 71.71 99.94 0.00 (207 kPaG) 9 20psig 1.39 23.3 97.50 681.25 73.40 99.98 0.00 (138 kPaG) 10 20 psig 0.9518.9 92.50 773.75 84.02 99.74 0.00 (138 kPaG) 11 20 psig 1.07 20.2 91.50865.25 77.01 99.86 0.00 (138 kPaG) 12 20 psig 1.61 24.11 86.00 951.2560.70 99.79 0.00 (138 kPaG) 13 20 psig 1.34 22.53 46.00 997.25 70.8499.76 0.00 (138 kPaG) 14 20 psig 1.95 24.50 6.50 1003.75 56.18 97.280.00 (138 kPaG) 15 20 psig 1.40 22.94 58.00 1061.75 66.98 99.69 0.00(138 kPaG) 16 20 psig 1.55 23.84 48.50 1110.25 63.61 99.98 0.00 (138kPaG) 17 20 psig 1.51 23.38 48.00 1158.25 64.21 99.98 0.00 (138 kPaG) 1820 psig 1.39 34.14 48.00 1206.25 52.92 99.85 0.00 (138 kPaG) 19 20 psig1.40 22.98 25.17 1231.42 64.97 99.98 0.00 (138 kPaG) 20 20 psig 1.2922.01 100 1331.42 73.38 99.97 0.00 (138 kPaG) 21 20 psig 1.27 21.96101.25 1432.67 67.59 99.94 0.00 (138 kPaG) 22 20 psig 1.51 24.05 23.001455.67 59.30 99.97 0.00 (138 kPaG) 23 20 psig 1.45 23.45 96.00 1551.6760.89 99.88 0.00 (138 kPaG) 24 20 psig 3.37 30.87 45.00 1596.67 24.2399.90 0.00 (138 kPaG) 25 20 psig 1.41 23.14 96.00 1692.67 67.87 99.960.00 (138 kPaG) 26 20 psig 1.43 23.36 96.00 1788.67 68.66 99.98 0.00(138 kPaG) 27 20 psig 1.19 21.61 96.00 1884.67 72.98 99.94 0.00 (138kPaG) 28 20 psig 1.60 24.34 100.00 1984.67 60.64 99.93 0.00 (138 kPaG)29 20 psig 1.37 23.00 67.25 2051.92 59.38 99.96 0.00 (138 kPaG)

Example 7: Separation of Trifluoroacetyl Iodide

In this Example, the separation of trifluoroacetyl iodide is described.A mixture containing about 80 wt. % trifluoroacetyl iodide, about 10 wt.% trifluoroacetyl chloride, about 5 wt. % hydrogen iodide, and about 5wt. % hydrogen chloride can be charged into a distillation column. Thedistillation column can include a 10 gallon reboiler, a 2-inch insidediameter 10-foot Pro-Pak® column from the Cannon Instrument Company,State College, Pa., and about 30 theoretical plates. The distillationcolumn can be equipped with temperature, absolute pressure, anddifferential pressure transmitters. The distillation can be run at apressure of about 300 kPaG and at a temperature of about 55° C., withhydrogen chloride taken off from the top of the column, and product fromthe bottom of the column.

Example 8: Manufacture of Trifluoroiodomethane from TrifluoroacetylIodide According to Equation 2 with an Activated Carbon Catalyst atAtmospheric Pressure

In this Example, the manufacture of trifluoroiodomethane fromtrifluoroacetyl iodide according to Equation 2 described above atatmospheric pressure is demonstrated. A mixture of 55 GC area %trifluoroacetyl iodide and 45 GC area % trifluoroacetyl chloride waspassed through a preheater and heated to a temperature of about 100° C.The heated reactants were passed through a stainless-steel tube ⅜ inch(9.5 mm) in diameter and 6 inches (152 mm) in length. The tube washeated to about 350° C., and purged with nitrogen for at least one hourbefore the experiment to drive off any water. The tube contained acatalyst of Norit-PK35 activated carbon for a contact time of about10-15 seconds. The output of the reactor was collected in a sample bagfor GC and GC-MS analyses.

Near complete conversion of trifluoroacetyl iodide totrifluoroiodomethane was observed. The ratio of trifluoroiodomethane tounreacted trifluoroacetyl iodide was 54:0.22 for an unreactedtrifluoroacetyl iodide of less than 0.5%, based on the GC area %measurements.

Example 9: Manufacture of Trifluoroiodomethane from TrifluoroacetylIodide According to Equation 2 without a Catalyst at Above AtmosphericPressure

In this Example, the manufacture of trifluoroiodomethane fromtrifluoroacetyl iodide according to Equation 2 described above atpressures above atmospheric pressure and without a separate catalyst isdemonstrated. A feed stream of at least 99.22 GC area % trifluoroacetyliodide was passed through a heated tube. The heated tube was acommercially pure (>99%) wrought nickel tube 0.5 inch (12.7 mm) indiameter with a heated zone 120 mm in length. The flow rate throughproduced a contact time of about 10 seconds. The tube contained nocatalyst. The feed had a contact time of about 10 seconds. A pressuretransducer and control valve at the outlet of the reactor were used tocontrol the pressure. The output of the reactor was collected in asample bag for GC and GC-MS analyses. The results are shown in Table 8.

Table 8 lists the reaction conditions (temperature, pressure) for eachof the twenty experiments. Table 8 also lists a conversion percentage ofthe trifluoroacetyl iodide and selectivity to trifluoroiodomethane foreach of the twenty experiments. Conversion and selectivity percentagesare based on GC area % data. Table 8 also lists the GC area % of theprimary organic compounds of interest corresponding to some of thetwenty-eight experiments

Considering the results of experiments 1-10 as shown in Table 8, theprocess described above in reference to Equation 2 operating at higherreaction pressures is able to produce trifluoroiodomethane with both ahigh conversion rate of the trifluoroacetyl iodide and high selectivityto forming trifluoroiodomethane. This effect was observed without theuse of a catalyst, other than any catalytic effect provided by thenickel reactor itself. While the use of a catalyst may provide improvedresults, particularly at lower reaction temperatures, not having toregenerate or replace a catalyst can provide for a more efficientprocess overall.

Considering the results of experiments 11-20 as shown in Table 8, is itshown that the improved results, without a catalyst, are particularlypronounced at higher pressures combined with higher temperatures, withimproved results shown at temperatures of 300° C. or greater at anoperating pressure at 200 psig (exp. 11-15) compared to operating atatmospheric pressure (exp. 16-20).

TABLE 8 Conversion Selectivity Exp. Temp. CF₃I CF₃COI CF₃COCI Others ofCF₃COI of CF₃I No. (° C.) Pressure (GC area %) (GC area %) (GC area %)(GC area %)) (%) (%) 1 350 0 psig 63 98.9 (kPaG) 2 350 50 psig 67.9931.62 0.17 0.22 68.3 99.4 (345 kPaG) 3 350 100 psig 87.79 11.90 0.130.18 88.1 99.6 (689 kPaG) 4 350 150 psig 92.78 6.88 0.13 0.21 93.1 99.6(1,034 kPaG) 5 350 200 psig 97.32 1.98 0.12 0.58 98.0 99.3 (1,379 kPaG)6 400 0 psig 78 99 (kPaG) 7 400 50 psig 99.1 0.55 0.10 0.25 99.4 99.6(345 kPaG) 8 400 100 psig 99.66 0.04 0.07 0.23 100 99.7 (689 kPaG) 9 400150 psig 99.73 0.00 0.08 0.19 100 99.7 (1,034 kPaG) 10 400 200 psig 99.80.00 0.20 0.00 100 99.8 (1,379 kPaG) 11 200 200 psig 3 (1,379 kPaG) 12250 200 psig 16 (1,379 kPaG) 13 300 200 psig 61 (1,379 kPaG) 14 350 200psig 97 (1,379 kPaG) 15 400 200 psig 100 (1,379 kPaG) 16 200 0 psig 0(kPaG) 17 250 0 psig 15 (kPaG) 18 300 0 psig 22 (kPaG) 19 350 0 psig 64(kPaG) 20 400 0 psig 79 (kPaG)

Example 10: Separation of Trifluoroiodomethane

In this Example, the separation of trifluoroiodomethane is described. Amixture containing about 85 wt. % trifluoroiodomethane, about 10 wt. %trifluoroacetyl iodide, and about 5 wt. % carbon monoxide can be chargedinto a distillation column. The distillation column can include a 10gallon reboiler at a temperature of about 25° C., a 2-inch insidediameter 10-foot Pro-Pak® column from the Cannon Instrument Company,State College, Pa., and about 30 theoretical plates. The distillationcolumn can be equipped with temperature, absolute pressure, anddifferential pressure transmitters. The distillation can be run at apressure of about 275 kPaG and a condenser at a temperature of about−13° C. to collect trifluoroiodomethane.

Aspects

Aspect 1 is a gas-phase process for producing trifluoroiodomethane, theprocess comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a first catalyst at a first reactiontemperature from about 25° C. to about 400° C. to produce anintermediate product stream comprising trifluoroacetyl iodide, andreacting the intermediate product stream in the presence of a secondcatalyst at a second reaction temperature from about 200° C. to about600° C. to produce a final product stream comprising thetrifluoroiodomethane.

Aspect 2 is the process of Aspect 1, wherein the step of reacting thereactant stream, the first reaction temperature is from about 40° C. toabout 120° C.

Aspect 3 is the process of Aspect 1, wherein the step of reacting thereactant stream, the first reaction temperature is from about 70° C. toabout 100° C.

Aspect 4 is the process of Aspect 1, wherein the step of reacting thereactant stream, the first reaction temperature is from about 80° C. toabout 100° C.

Aspect 5 is the process of any of Aspects 1-4, wherein in the providingstep, the reactant stream comprises less than about 500 ppm by weight ofoxygen.

Aspect 6 is the process of any of Aspects 1-4, wherein in the providingstep, the reactant stream comprises less than about 100 ppm by weight ofoxygen.

Aspect 7 is the process of any of Aspects 1-4, wherein in the providingstep, the reactant stream comprises less than about 10 ppm by weight ofoxygen.

Aspect 8 is the process of any of Aspects 1-4, wherein in the providingstep, the reactant stream comprises less than about 1 ppm by weight ofoxygen.

Aspect 9 is the process of any of Aspects 1-8, wherein in the providingstep, the hydrogen iodide comprises less than about 500 ppm by weight ofwater.

Aspect 10 is the process of any of Aspects 1-8, wherein in the providingstep, the hydrogen iodide comprises less than about 100 ppm by weight ofwater.

Aspect 11 is the process of any of Aspects 1-8, wherein in the providingstep, the hydrogen iodide comprises less than about 10 ppm by weight ofwater.

Aspect 12 is the process of any of Aspects 1-8, wherein in the providingstep, the hydrogen iodide comprises less than about 1 ppm by weight ofwater.

Aspect 13 is the process of any of Aspects 1-12, wherein in theproviding step, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.1:1 to about 10:1.

Aspect 14 is the process of any of Aspects 1-12, wherein in theproviding step, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.5:1 to about 2.0:1.

Aspect 15 is the process of any of Aspects 1-12, wherein in theproviding step, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.6:1 to about 1.2:1.

Aspect 16 is the process of any of Aspects 1-12, wherein in theproviding step, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.7:1 to about 1.0:1.

Aspect 17 is the process of any of Aspects 1-16, wherein in the step ofreacting the reactant stream, the first catalyst comprises activatedcarbon, meso carbon, stainless steel, nickel, nickel-chromium alloy,nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina,platinum, palladium, metal carbides, non-metal carbides or combinationsthereof.

Aspect 18 is the process of any of Aspects 1-16, wherein the firstcatalyst comprises activated carbon, meso carbon, stainless steel,platinum on a support, palladium on a support, silicon carbide, orcombinations thereof.

Aspect 19 is the process of any of Aspects 1-16, wherein the firstcatalyst comprises platinum on a support, palladium on a support,activated carbon, silicon carbide, or combinations thereof.

Aspect 20 is the process of any of Aspects 1-16, wherein the firstcatalyst comprises activated carbon or silicon carbide.

Aspect 21 is the process of any of Aspects 1-20, wherein in the step ofreacting the reactant stream, the reactant stream may be in contact withthe first catalyst for a contact time from about 0.1 seconds to about300 seconds.

Aspect 22 is the process of any of Aspects 1-20, wherein in the step ofreacting the reactant stream, the reactant stream may be in contact withthe first catalyst for a contact time from about 5 seconds to about 60seconds.

Aspect 23 is the process of any of Aspects 1-20, wherein in the step ofreacting the reactant stream, the reactant stream may be in contact withthe first catalyst for a contact time from about 10 seconds to about 40seconds.

Aspect 24 is the process of any of Aspects 1-20, wherein in the step ofreacting the reactant stream, the reactant stream may be in contact withthe first catalyst for a contact time from about 15 seconds to about 35seconds.

Aspect 25 is the process of any of Aspects 1-24, wherein in the step ofreacting the reactant stream is at a pressure from about atmosphericpressure to about 300 psig (2,068 kPaG).

Aspect 26 is the process of any of Aspects 1-24, wherein in the step ofreacting the reactant stream is at a pressure from about 5 psig (34kPaG) to about 200 psig (1,379 kPaG).

Aspect 27 is the process of any of Aspects 1-24, wherein in the step ofreacting the reactant stream is at a pressure from about 10 psig (69kPaG) to about 150 psig (1,034 kPaG).

Aspect 28 is the process of any of Aspects 1-24, wherein in the step ofreacting the reactant stream is at a pressure from about 20 psig (138kPaG) to about 100 psig (689 kPaG).

Aspect 29 is the process of any of Aspects 1-28, wherein in the step ofreacting the intermediate product stream, the second reactiontemperature is from about 250° C. to about 500° C.

Aspect 30 is the process of any of Aspects 1-28, wherein in the step ofreacting the intermediate product stream, the second reactiontemperature is from about 300° C. to about 400° C.

Aspect 31 is the process of any of Aspects 1-28, wherein in the step ofreacting the intermediate product stream, the second reactiontemperature is from about 300° C. to about 350° C.

Aspect 32 is the process of any of Aspects 1-31, wherein in the step ofreacting the intermediate product stream, the intermediate productstream may be in contact with the second catalyst for a contact timefrom about 0.1 seconds to about 300 seconds.

Aspect 33 is the process of any of Aspects 1-31, wherein in the step ofreacting the intermediate product stream, the intermediate productstream may be in contact with the second catalyst for a contact timefrom about 1 seconds to about 60 seconds.

Aspect 34 is the process of any of Aspects 1-31, wherein in the step ofreacting the intermediate product stream, the intermediate productstream may be in contact with the second catalyst for a contact timefrom about 2 seconds to about 50 seconds.

Aspect 35 is the process of any of Aspects 1-31, wherein in the step ofreacting the intermediate product, the intermediate product stream maybe in contact with the second catalyst for a contact time from about 3seconds to about 30 seconds.

Aspect 36 is the process of any of Aspects 1-35, wherein in the step ofreacting the intermediate product stream, the second catalyst comprisesstainless steel, nickel, nickel-chromium alloy,nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina,silicon carbide, platinum, palladium, rhenium, activated carbon, mesocarbon or combinations thereof.

Aspect 37 is the process of any of Aspects 1-35, wherein in the step ofreacting the intermediate product stream, the second catalyst comprisesactivated carbon, about 0.1 wt. % to about 1 wt. % platinum on asupport, about 0.1 wt. % to about 1 wt. % palladium on a support, about0.1 wt. % to about 1 wt. % rhenium on a support, or combinationsthereof.

Aspect 38 is the process of any of Aspects 1-35, wherein in the step ofreacting the intermediate product stream, the second catalyst comprisesactivated carbon or about 0.3 wt. % to about 0.7 wt. % palladium on asupport.

Aspect 39 is the process of any of Aspects 1-35, wherein in the step ofreacting the intermediate product stream, the second catalyst comprisesactivated carbon.

Aspect 40 is the process of any of Aspects 1-35, wherein in the step ofreacting the intermediate product stream, the second catalyst consistsof surfaces of a reactor in contact with the intermediate productstream.

Aspect 41 is the process of any of Aspects 1-40, wherein the step ofreacting the intermediate product stream is at a pressure from about 5psig (34 kPaG) to about 300 psig (2,068 kPaG).

Aspect 42 is a gas-phase process for producing trifluoroiodomethane, theprocess comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a first catalyst at a first reactiontemperature from about 25° C. to about 400° C., at a pressure from aboutatmospheric pressure to about 300 psig (2,068 kPaG) for a first contacttime of about 0.1 seconds to about 300 seconds to produce anintermediate product stream comprising trifluoroacetyl iodide, andreacting the intermediate product stream in the presence of a secondcatalyst at a second reaction temperature from about 200° C. to about600° C. for a second contact time of about 0.1 seconds to about 300seconds to produce a final product stream comprising thetrifluoroiodomethane, wherein a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.1:1 to about 10:1, the firstcatalyst comprises activated carbon, meso carbon, stainless steel,nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy,nickel-copper alloy, copper, alumina, platinum, palladium, metalcarbides, non-metal carbides or combinations thereof, the secondcatalyst comprises stainless steel, nickel, nickel-chromium alloy,nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina,silicon carbide, platinum, palladium, rhenium, activated carbon, mesocarbon or combinations thereof.

Aspect 43 is a gas-phase process for producing trifluoroiodomethane, theprocess comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a first catalyst at a first reactiontemperature from about 40° C. to about 120° C., at a pressure from about5 psig (34 kPaG) to about 200 psig (1,379 kPaG) for a first contact timeof about 5 seconds to about 60 seconds to produce an intermediateproduct stream comprising trifluoroacetyl iodide, and reacting theintermediate product stream in the presence of a second catalyst at asecond reaction temperature from about 250° C. to about 500° C. for asecond contact time of about 1 second to about 60 seconds to produce afinal product stream comprising the trifluoroiodomethane, wherein a moleratio of the hydrogen iodide to the trifluoroacetyl halide is from about0.5:1 to about 2:1, the first catalyst comprises activated carbon, mesocarbon, stainless steel, platinum on a support, palladium on a support,silicon carbide, or combinations thereof, the second catalyst comprisesactivated carbon, about 0.1 wt. % to about 1 wt. % platinum on asupport, about 0.1 wt. % to about 1 wt. % palladium on a support, about0.1 wt. % to about 1 wt. % rhenium on a support, or combinationsthereof.

Aspect 44 is a gas-phase process for producing trifluoroiodomethane, theprocess comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a first catalyst at a first reactiontemperature from about 70° C. to about 100° C., at a pressure from about10 psig (69 kPaG) to about 150 psig (1,034 kPaG) for a first contacttime of about 10 seconds to about 40 seconds to produce an intermediateproduct stream comprising trifluoroacetyl iodide, and reacting theintermediate product stream in the presence of a second catalyst at asecond reaction temperature from about 300° C. to about 400° C. for asecond contact time of about 2 seconds to about 50 seconds to produce afinal product stream comprising the trifluoroiodomethane, wherein a moleratio of the hydrogen iodide to the trifluoroacetyl halide is from about0.6:1 to about 1.2:1, wherein the first catalyst comprises platinum on asupport, palladium on a support, activated carbon, silicon carbide, orcombinations thereof, the second catalyst comprises activated carbon orabout 0.3 wt. % to about 0.7 wt. % palladium on a support.

Aspect 45 is a gas-phase process for producing trifluoroiodomethane, theprocess comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a first catalyst at a first reactiontemperature from about 80° C. to about 100° C., at a pressure from about10 psig (69 kPaG) to about 150 psig (1,034 kPaG) for a first contacttime of about 15 seconds to about 35 seconds to produce an intermediateproduct stream comprising trifluoroacetyl iodide, and reacting theintermediate product stream in the presence of a second catalyst at asecond reaction temperature from about 300° C. to about 350° C. for asecond contact time of about 3 seconds to about 30 seconds to produce afinal product stream comprising the trifluoroiodomethane, wherein a moleratio of the hydrogen iodide to the trifluoroacetyl halide is from about0.7:1 to about 1.0:1, wherein the first catalyst comprises platinum on asupport, palladium on a support, silicon carbide, or combinationsthereof, the second catalyst comprises activated carbon.

Aspect 46 is the process of any of Aspects 42-47, wherein in theproviding step, the reactant stream comprises less than about 500 ppm byweight of oxygen and the hydrogen iodide comprises less than about 500ppm by weight of water.

Aspect 47 is the process of any of Aspects 42-47, wherein in theproviding step, the reactant stream comprises less than about 100 ppm byweight of oxygen and the hydrogen iodide comprises less than about 100ppm by weight of water.

Aspect 48 is the process of any of Aspects 42-47, wherein in theproviding step, the reactant stream comprises less than about 10 ppm byweight of oxygen and the hydrogen iodide comprises less than about 10ppm by weight of water.

Aspect 49 is the process of any of Aspects 42-47, wherein in theproviding step, the reactant stream comprises less than about 1 ppm byweight of oxygen and the hydrogen iodide comprises less than about 1 ppmby weight of water.

Aspect 50 is the process of any of Aspects 1-49, wherein in theproviding step, the trifluoroacetyl halide comprises trifluoroacetylchloride.

Aspect 51 is the process of any of Aspects 1-50, wherein organiccompounds in the intermediate product stream comprise, in GC area % oftotal organic compounds, from about 10% to about 99% trifluoroacetyliodide, from about 1% to about 90% unreacted trifluoroacetyl halide,less than about 0.010% trifluoroiodomethane, and less than about 15%organic compounds other than trifluoroacetyl iodide, trifluoroacetylhalide, and trifluoroiodomethane.

Aspect 52 is the process of any of Aspects 1-50, wherein organiccompounds in the intermediate product stream comprise, in GC area % oftotal organic compounds, from about 50% to about 99% trifluoroacetyliodide, from about 1% to about 50% unreacted trifluoroacetyl halide,less than about 0.002% trifluoroiodomethane, and less than about 8%organic compounds other than trifluoroacetyl iodide, trifluoroacetylhalide, and trifluoroiodomethane.

Aspect 53 is the process of any of Aspects 1-50, wherein organiccompounds in the intermediate product stream comprise, in GC area % oftotal organic compounds, from about 60% to about 99% trifluoroacetyliodide, from about 1% to about 40% unreacted trifluoroacetyl halide,less than about 0.001% trifluoroiodomethane, and less than about 4%organic compounds other than trifluoroacetyl iodide, trifluoroacetylhalide, and trifluoroiodomethane.

Aspect 54 is the process of any of Aspects 1-50, wherein organiccompounds in the intermediate product stream comprise, in GC area % oftotal organic compounds, from about 70% to about 99% trifluoroacetyliodide, from about 1% to about 30% unreacted trifluoroacetyl halide,less than about 0.0005% trifluoroiodomethane, and less than about 2%organic compounds other than trifluoroacetyl iodide, trifluoroacetylhalide, and trifluoroiodomethane.

Aspect 55 is the process of any of Aspects 1-54, further comprising theadditional steps of separating unreacted trifluoroacetyl halide from theintermediate product stream, returning the separated trifluoroacetylhalide to the reactant stream, separating unreacted hydrogen iodide fromthe intermediate product stream, returning the unreacted hydrogen iodideto the reactant stream, separating unreacted trifluoroacetyl iodide fromthe final product stream and returning the separated unreactedtrifluoroacetyl iodide to the intermediate product stream.

Aspect 56 is a gas-phase process for producing trifluoroacetyl iodide,the process comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, and reacting thereactant stream in the presence of a first catalyst at a reactiontemperature from about 25° C. to about 400° C. to produce a productstream comprising the trifluoroacetyl iodide.

Aspect 57 is the process of Aspect 56, wherein the step of reacting thereactant stream, the reaction temperature is from about 40° C. to about120° C.

Aspect 58 is the process of Aspect 56, wherein the step of reacting thereactant stream, the reaction temperature is from about 70° C. to about100° C.

Aspect 59 is the process of Aspect 56, wherein the step of reacting thereactant stream, the reaction temperature is from about 80° C. to about100° C.

Aspect 60 is the process of any of Aspects 56-59, wherein in theproviding step, the reactant stream comprises less than about 500 ppm byweight of oxygen.

Aspect 61 is the process of any of Aspects 56-59, wherein in theproviding step, the reactant stream comprises less than about 100 ppm byweight of oxygen.

Aspect 62 is the process of any of Aspects 56-59, wherein in theproviding step, the reactant stream comprises less than about 10 ppm byweight of oxygen.

Aspect 63 is the process of any of Aspects 56-59, wherein in theproviding step, the reactant stream comprises less than about 1 ppm byweight of oxygen.

Aspect 64 is the process of any of Aspects 56-63, wherein in theproviding step, the hydrogen iodide comprises less than about 500 ppm byweight of water.

Aspect 65 is the process of any of Aspects 56-63, wherein in theproviding step, the hydrogen iodide comprises less than about 100 ppm byweight of water.

Aspect 66 is the process of any of Aspects 56-63, wherein in theproviding step, the hydrogen iodide comprises less than about 10 ppm byweight of water.

Aspect 67 is the process of any of Aspects 56-63, wherein in theproviding step, the hydrogen iodide comprises less than about 1 ppm byweight of water.

Aspect 68 is the process of any of Aspects 56-67, wherein in theproviding step, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.1:1 to about 10:1.

Aspect 69 is the process of any of Aspects 56-67, wherein in theproviding step, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.5:1 to about 2.0:1.

Aspect 70 is the process of any of Aspects 56-67, wherein in theproviding step, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.6:1 to about 1.2:1.

Aspect 71 is the process of any of Aspects 56-67, wherein in theproviding step, a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.7:1 to about 1.0:1.

Aspect 72 is the process of any of Aspects 56-71, wherein in the step ofreacting the reactant stream, the catalyst comprises activated carbon,meso carbon, stainless steel, nickel, nickel-chromium alloy,nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina,platinum, palladium, metal carbides, non-metal carbides or combinationsthereof.

Aspect 73 is the process of any of Aspects 56-71, wherein the catalystcomprises activated carbon, meso carbon, stainless steel, platinum on asupport, palladium on a support, silicon carbide, or combinationsthereof.

Aspect 74 is the process of any of Aspects 56-71, wherein the catalystcomprises platinum on a support, palladium on a support, activatedcarbon, silicon carbide, or combinations thereof.

Aspect 75 is the process of any of Aspects 56-71, wherein the catalystcomprises activated carbon or silicon carbide.

Aspect 75 is the process of any of Aspects 56-75, wherein in the step ofreacting the reactant stream, the reactant stream may be in contact withthe catalyst for a contact time from about 0.1 seconds to about 300seconds.

Aspect 77 is the process of any of Aspects 56-75, wherein in the step ofreacting the reactant stream, the reactant stream may be in contact withthe catalyst for a contact time from about 5 seconds to about 60seconds.

Aspect 78 is the process of any of Aspects 56-75, wherein in the step ofreacting the reactant stream, the reactant stream may be in contact withthe catalyst for a contact time from about 10 seconds to about 40seconds.

Aspect 79 is the process of any of Aspects 56-75, wherein in the step ofreacting the reactant stream, the reactant stream may be in contact withthe catalyst for a contact time from about 15 seconds to about 35seconds.

Aspect 80 is the process of any of Aspects 56-79, wherein in the step ofreacting the reactant stream is at a pressure from about atmosphericpressure to about 300 psig (2,068 kPaG).

Aspect 81 is the process of any of Aspects 56-79, wherein in the step ofreacting the reactant stream is at a pressure from about 5 psig (34kPaG) to about 200 psig (1,379 kPaG).

Aspect 82 is the process of any of Aspects 56-79, wherein in the step ofreacting the reactant stream is at a pressure from about 10 psig (69kPaG) to about 150 psig (1,034 kPaG).

Aspect 83 is the process of any of Aspects 56-79, wherein in the step ofreacting the reactant stream is at a pressure from about 20 psig (138kPaG) to about 100 psig (689 kPaG).

Aspect 84 is a gas-phase process for producing trifluoroacetyl iodide,the process comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a catalyst at a reaction temperature fromabout 25° C. to about 400° C., at a pressure from about atmosphericpressure to about 300 psig (2,068 kPaG) for a contact time of about 0.1seconds to about 300 seconds to produce a product stream comprising thetrifluoroacetyl iodide, wherein a mole ratio of the hydrogen iodide tothe trifluoroacetyl halide is from about 0.1:1 to about 10:1, and thecatalyst comprises activated carbon, meso carbon, stainless steel,nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy,nickel-copper alloy, copper, alumina, platinum, palladium, metalcarbides, non-metal carbides or combinations thereof.

Aspect 85 is a gas-phase process for producing trifluoroacetyl iodide,the process comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a catalyst at a reaction temperature fromabout 40° C. to about 120° C., at a pressure from about 5 psig (34 kPaG)to about 200 psig (1,379 kPaG) for a contact time of about 5 seconds toabout 60 seconds to produce a product stream comprising trifluoroacetyliodide, wherein a mole ratio of the hydrogen iodide to thetrifluoroacetyl halide is from about 0.5:1 to about 2:1 and the catalystcomprises activated carbon, meso carbon, stainless steel, platinum on asupport, palladium on a support, silicon carbide, or combinationsthereof.

Aspect 86 is a gas-phase process for producing trifluoroacetyl iodide,the process comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a catalyst at a reaction temperature fromabout 70° C. to about 100° C., at a pressure from about 10 psig (69kPaG) to about 150 psig (1,034 kPaG) for a contact time of about 10seconds to about 40 seconds to produce a product stream comprisingtrifluoroacetyl iodide, wherein a mole ratio of the hydrogen iodide tothe trifluoroacetyl halide is from about 0.6:1 to about 1.2:1 and thecatalyst comprises platinum on a support, palladium on a support,activated carbon, silicon carbide, or combinations thereof.

Aspect 87 is a gas-phase process for producing trifluoroacetyl iodide,the process comprising providing a reactant stream comprising hydrogeniodide and at least one trifluoroacetyl halide selected from the groupconsisting of trifluoroacetyl chloride, trifluoroacetyl fluoride,trifluoroacetyl bromide, and combinations thereof, reacting the reactantstream in the presence of a catalyst at a reaction temperature fromabout 80° C. to about 100° C., at a pressure from about 10 psig (69kPaG) to about 150 psig (1,034 kPaG) for a contact time of about 15seconds to about 35 seconds to produce a product stream comprisingtrifluoroacetyl iodide, wherein a mole ratio of the hydrogen iodide tothe trifluoroacetyl halide is from about 0.7:1 to about 1.0:1 and thecatalyst comprises platinum on a support, palladium on a support,silicon carbide, or combinations thereof.

Aspect 88 is the process of any of Aspects 84-87, wherein in theproviding step, the reactant stream comprises less than about 500 ppm byweight of oxygen and the hydrogen iodide comprises less than about 500ppm by weight of water.

Aspect 89 is the process of any of Aspects 84-87, wherein in theproviding step, the reactant stream comprises less than about 100 ppm byweight of oxygen and the hydrogen iodide comprises less than about 100ppm by weight of water.

Aspect 90 is the process of any of Aspects 84-87, wherein in theproviding step, the reactant stream comprises less than about 10 ppm byweight of oxygen and the hydrogen iodide comprises less than about 10ppm by weight of water.

Aspect 91 is the process of any of Aspects 84-87, wherein in theproviding step, the reactant stream comprises less than about 1 ppm byweight of oxygen and the hydrogen iodide comprises less than about 1 ppmby weight of water.

Aspect 92 is the process of any of Aspects 56-91, wherein in theproviding step, the trifluoroacetyl halide comprises trifluoroacetylchloride.

Aspect 93 is a composition comprising at least 98 wt. % oftrifluoroacetyl iodide, and from about 1 ppm to about 20,000 ppm (about2 wt. %) in total of compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 94 is a composition comprising at least 99 wt. % oftrifluoroacetyl iodide, and from 1 ppm to 10,000 ppm (1 wt. %) in totalof compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 95 is a composition comprising at least 99.5 wt. % oftrifluoroacetyl iodide, and from 1 ppm to 5,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 96 is a composition comprising at least 99.7 wt. % oftrifluoroacetyl iodide, and from 1 ppm to 3,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 97 is a composition consisting essentially of at least 98 wt. %of trifluoroacetyl iodide, and from about 1 ppm to about 20,000 ppm(about 2 wt. %) in total of compounds selected from the group consistingof chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane.

Aspect 98 is a composition consisting essentially of at least 99 wt. %of trifluoroacetyl iodide, and from 1 ppm to 10,000 ppm (1 wt. %) intotal of compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 99 is a composition consisting essentially of at least 99.5 wt. %of trifluoroacetyl iodide, and from 1 ppm to 5,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 100 is a composition consisting essentially of at least 99.7 wt.% of trifluoroacetyl iodide, and from 1 ppm to 3,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 101 is a composition consisting of at least 98 wt. % oftrifluoroacetyl iodide, and from about 1 ppm to about 20,000 ppm (about2 wt. %) in total of compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 102 is a composition consisting of at least 99 wt. % oftrifluoroacetyl iodide, and from 1 ppm to 10,000 ppm (1 wt. %) in totalof compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 103 is a composition consisting of at least 99.5 wt. % oftrifluoroacetyl iodide, and from 1 ppm to 5,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 104 is a composition consisting of at least 99.7 wt. % oftrifluoroacetyl iodide, and from 1 ppm to 3,000 ppm in total ofcompounds selected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.

Aspect 105 is a composition comprising at least 99 wt. % oftrifluoroiodomethane, from 1 ppm to 500 ppm chlorotrifluoroethane, lessthan 500 ppm hexafluoroethane, less than 500 ppm trifluoromethane, lessthan 100 ppm carbon monoxide, less than 1 ppm hydrogen chloride and from1 ppm to 500 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 106 is a composition comprising at least 99.5 wt. % oftrifluoroiodomethane, from 1 ppm to 250 ppm chlorotrifluoroethane, lessthan 250 ppm hexafluoroethane, less than 250 ppm trifluoromethane, lessthan 50 ppm carbon monoxide, less than 0.5 ppm hydrogen chloride andfrom 1 ppm to 250 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 107 is a composition comprising at least 99.7 wt. % oftrifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane, lessthan 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane, lessthan 20 ppm carbon monoxide, less than 0.2 ppm hydrogen chloride andfrom 1 ppm to 100 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 108 is a composition comprising at least 99.9 wt. % oftrifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane, lessthan 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane, lessthan 20 ppm carbon monoxide, less than 0.2 ppm hydrogen chloride andfrom 1 ppm to 100 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 109 is a composition consisting essentially of at least 99 wt. %of trifluoroiodomethane, from 1 ppm to 500 ppm chlorotrifluoroethane,less than 500 ppm hexafluoroethane, less than 500 ppm trifluoromethane,less than 100 ppm carbon monoxide, less than 1 ppm hydrogen chloride andfrom 1 ppm to 500 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 110 is a composition consisting essentially of at least 99.5 wt.% of trifluoroiodomethane, from 1 ppm to 250 ppm chlorotrifluoroethane,less than 250 ppm hexafluoroethane, less than 250 ppm trifluoromethane,less than 50 ppm carbon monoxide, less than 0.5 ppm hydrogen chlorideand from 1 ppm to 250 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 111 is a composition consisting essentially of at least 99.7 wt.% of trifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane,less than 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane,less than 20 ppm carbon monoxide, less than 0.2 ppm hydrogen chlorideand from 1 ppm to 100 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 112 is a composition consisting essentially of at least 99.9 wt.% of trifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane,less than 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane,less than 20 ppm carbon monoxide, less than 0.2 ppm hydrogen chlorideand from 1 ppm to 100 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 109 is a composition consisting of at least 99 wt. % oftrifluoroiodomethane, from 1 ppm to 500 ppm chlorotrifluoroethane, lessthan 500 ppm hexafluoroethane, less than 500 ppm trifluoromethane, lessthan 100 ppm carbon monoxide, less than 1 ppm hydrogen chloride and from1 ppm to 500 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 110 is a composition consisting of at least 99.5 wt. % oftrifluoroiodomethane, from 1 ppm to 250 ppm chlorotrifluoroethane, lessthan 250 ppm hexafluoroethane, less than 250 ppm trifluoromethane, lessthan 50 ppm carbon monoxide, less than 0.5 ppm hydrogen chloride andfrom 1 ppm to 250 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 111 is a composition consisting of at least 99.7 wt. % oftrifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane, lessthan 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane, lessthan 20 ppm carbon monoxide, less than 0.2 ppm hydrogen chloride andfrom 1 ppm to 100 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 112 is a composition consisting of at least 99.9 wt. % oftrifluoroiodomethane, from 1 ppm to 100 ppm chlorotrifluoroethane, lessthan 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane, lessthan 20 ppm carbon monoxide, less than 0.2 ppm hydrogen chloride andfrom 1 ppm to 100 ppm in total of compounds selected from the groupconsisting of trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetaldehyde, and trifluoroacetyl chloride.

Aspect 113 is a gas-phase process for producing trifluoroiodomethane,the process comprising providing a reactant stream comprisingtrifluoroacetyl iodide, and reacting the reactant stream in the presenceof a catalyst at a reaction temperature from about 200° C. to about 600°C. to produce a product stream comprising the trifluoroiodomethane.

Aspect 114 is the process of Aspect 113, wherein in the step of reactingthe reactant stream, the reaction temperature is from about 250° C. toabout 500° C.

Aspect 115 is the process of Aspect 113, wherein in the step of reactingthe reactant stream, the reaction temperature is from about 300° C. toabout 400° C.

Aspect 116 is the process of Aspect 113, wherein in the step of reactingthe reactant stream, the reaction temperature is from about 300° C. toabout 350° C.

Aspect 117 is the process of any of Aspects 113-116, wherein in the stepof reacting the reactant stream, the reactant stream may be in contactwith the catalyst for a contact time from about 0.1 seconds to about 300seconds.

Aspect 118 is the process of any of Aspects 113-116, wherein in the stepof reacting the reactant stream, the reactant stream may be in contactwith the catalyst for a contact time from about 1 seconds to about 60seconds.

Aspect 119 is the process of any of Aspects 113-116, wherein in the stepof reacting the reactant stream, the reactant stream may be in contactwith the catalyst for a contact time from about 2 seconds to about 50seconds.

Aspect 120 is the process of any of Aspects 113-116, wherein in the stepof reacting the reactant stream, the reactant stream may be in contactwith the catalyst for a contact time from about 3 seconds to about 30seconds.

Aspect 121 is the process of any of Aspects 113-120, wherein in the stepof reacting the reactant stream, the catalyst comprises stainless steel,nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy,nickel-copper alloy, copper, alumina, silicon carbide, platinum,palladium, rhenium, activated carbon, meso carbon or combinationsthereof.

Aspect 122 is the process of any of Aspects 113-120, wherein in the stepof reacting the reactant stream, the catalyst comprises activatedcarbon, about 0.1 wt. % to about 1 wt. % platinum on a support, about0.1 wt. % to about 1 wt. % palladium on a support, about 0.1 wt. % toabout 1 wt. % rhenium on a support, or combinations thereof.

Aspect 123 is the process of any of Aspects 113-120, wherein in the stepof reacting the reactant stream, the catalyst comprises activated carbonor about 0.3 wt. % to about 0.7 wt. % palladium on a support.

Aspect 124 is the process of any of Aspects 113-120, wherein in the stepof reacting the reactant stream, the catalyst comprises activatedcarbon.

Aspect 125 is the process of any of Aspects 113-120, wherein in the stepof reacting the reactant stream, the catalyst consists of surfaces of areactor in contact with the reactant stream.

Aspect 126 is the process of any of Aspects 113-125, wherein the step ofreacting the reactant stream is at a pressure from about 5 psig (34kPaG) to about 300 psig (2,068 kPaG).

Aspect 127 is a gas-phase process for producing trifluoroiodomethane,the process comprising providing a reactant stream comprisingtrifluoroacetyl iodide, and reacting the reactant stream in the presenceof a catalyst at a reaction temperature from about 200° C. to about 600°C. for a contact time of about 0.1 seconds to about 300 seconds toproduce a product stream comprising the trifluoroiodomethane, whereinthe catalyst comprises stainless steel, nickel, nickel-chromium alloy,nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina,silicon carbide, platinum, palladium, rhenium, activated carbon, mesocarbon or combinations thereof.

Aspect 128 is a gas-phase process for producing trifluoroiodomethane,the process comprising providing a reactant stream comprisingtrifluoroacetyl iodide, and reacting the reactant stream in the presenceof a catalyst at a reaction temperature from about 250° C. to about 500°C. for a contact time of about 1 second to about 60 seconds to produce aproduct stream comprising the trifluoroiodomethane, wherein the catalystcomprises activated carbon, about 0.1 wt. % to about 1 wt. % platinum ona support, about 0.1 wt. % to about 1 wt. % palladium on a support,about 0.1 wt. % to about 1 wt. % rhenium on a support, or combinationsthereof.

Aspect 129 is a gas-phase process for producing trifluoroiodomethane,the process comprising providing a reactant stream comprisingtrifluoroacetyl iodide, and reacting the reactant stream in the presenceof a catalyst at a reaction temperature from about 300° C. to about 400°C. for a contact time of about 2 seconds to about 50 seconds to producea product stream comprising the trifluoroiodomethane, wherein thecatalyst comprises activated carbon or about 0.3 wt. % to about 0.7 wt.% palladium on a support.

Aspect 130 is a gas-phase process for producing trifluoroiodomethane,the process comprising providing a reactant stream comprisingtrifluoroacetyl iodide, and reacting the reactant stream in the presenceof a catalyst at a reaction temperature from about 300° C. to about 350°C. for a contact time of about 3 seconds to about 30 seconds to producea product stream comprising the trifluoroiodomethane, wherein thecatalyst comprises activated carbon.

What is claimed is:
 1. A composition comprising: at least 99 wt. % oftrifluoroiodomethane; less than 500 ppm hexafluoroethane; less than 500ppm trifluoromethane; less than 100 ppm carbon monoxide; less than 1 ppmhydrogen chloride; and from 1 ppm to 500 ppm in total of compoundsselected from the group consisting of trifluoroacetyl fluoride,hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetylchloride.
 2. The composition of claim 1 comprising: at least 99.5 wt. %of trifluoroiodomethane; less than 250 ppm hexafluoroethane; less than250 ppm trifluoromethane; less than 50 ppm carbon monoxide; less than0.5 ppm hydrogen chloride; and from 1 ppm to 250 ppm in total ofcompounds selected from the group consisting of trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetaldehyde, andtrifluoroacetyl chloride.
 3. The composition of claim 1 comprising: atleast 99.7 wt. % of trifluoroiodomethane; less than 100 ppmhexafluoroethane; less than 100 ppm trifluoromethane; less than 20 ppmcarbon monoxide; less than 0.2 ppm hydrogen chloride; and from 1 ppm to100 ppm in total of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride.
 4. The composition of claim 1 comprising:at least 99.9 wt. % of trifluoroiodomethane; less than 100 ppmhexafluoroethane; less than 100 ppm trifluoromethane; less than 20 ppmcarbon monoxide; less than 0.2 ppm hydrogen chloride; and from 1 ppm to100 ppm in total of compounds selected from the group consisting oftrifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde,and trifluoroacetyl chloride.
 5. A composition comprising: at least 98wt. % of trifluoroacetyl iodide, and from about 1 ppm to about 20,000ppm in total of compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.
 6. The composition of claim 5 consistingessentially of: at least 98 wt. % of trifluoroacetyl iodide, and fromabout 1 ppm to about 20,000 ppm in total of compounds selected from thegroup consisting of chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane.
 7. The composition ofclaim 5 comprising: at least 99 wt. % of trifluoroacetyl iodide, andfrom about 1 ppm to about 10,000 ppm in total of compounds selected fromthe group consisting of chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane.
 8. The composition ofclaim 7 consisting essentially of: at least 99 wt. % of trifluoroacetyliodide, and from about 1 ppm to about 10,000 ppm in total of compoundsselected from the group consisting of chlorotrifluoroethane,trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetylfluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.
 9. The composition of claim 5 comprising: atleast 99.5 wt. % of trifluoroacetyl iodide, and from about 1 ppm toabout 5,000 ppm in total of compounds selected from the group consistingof chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane.
 10. The composition ofclaim 9 consisting essentially of: at least 99.5 wt. % oftrifluoroacetyl iodide, and from about 1 ppm to about 5,000 ppm in totalof compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.
 11. The composition of claim 5 comprising: atleast 99.7 wt. % of trifluoroacetyl iodide, and from about 1 ppm toabout 3,000 ppm in total of compounds selected from the group consistingof chlorotrifluoroethane, trifluoroacetyl chloride,iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone,trifluoroacetic acid and chlorotrifluoromethane.
 12. The composition ofclaim 11 consisting essentially of: at least 99.7 wt. % oftrifluoroacetyl iodide, and from about 1 ppm to about 3,000 ppm in totalof compounds selected from the group consisting ofchlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane,trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid andchlorotrifluoromethane.